Jilek, Jiri O.'s team published research in Chemicke Listy pro Vedu a Prumysl in 46

Jilek, Jiri O. published the artcileSynthetic spasmolytics. V. Cyclic analogs of compounds of the 3,3-diphenylpropylamine series, Computed Properties of 1949-41-3, the publication is Chemicke Listy pro Vedu a Prumysl (1952), 292-6, database is CAplus.

cf. C.A. 46, 8004h. Amino ketones obtained by the Mannich reaction with 1-indanone (I), 3,4-dihydro-1(2H)-naphthalenone (II), and 6,7,8,9-tetrahydro-5H-cycloheptabenzen-5-one (III) were treated with PhMgBr (IV), and the corresponding carbinols dehydrated. Attempts to hydrogenate the olefins thus obtained resulted in hydrogenolysis. Some of the products have spasmolytic effects, lower than those of their open-chain analogs. I (17 g.), 40 g. C₅H₁₀NH.HCl (V), 3.9 g. paraformaldehyde (VI), and 100 mL. EtOH were refluxed 8 h., 1 more g. VI was added, the mixture refluxed 2 h., allowed to stand overnight, the EtOH distilled off, the residue dissolved in 300 mL. H₂O, the unreacted I extracted with C₆H₆, the aqueous layer made alk., the bases extracted with C₆H₆, the residue (21 g.) dissolved in 200 mL. ether, and 18 g. (53%) HCl salt, m. 213-15° (from EtOH-Me₂CO), of 2-(1-piperidylmethyl)-1-indanone (VII) precipitated with 10% EtOH solution of HCl. Analogously, 35.5 g. (58%) 3,4-dihydro-2-(1-piperidyl)methyl-l(2H)-naphthalenone (VIII) HCl salt, m. 228-30°, was obtained from 78 g. II (32 g. recovered unchanged), 71 g. V, and 15 + 1 g. VI. 6,7,8,9-Tetrahydro-6-(1-piperidylmethyl)-5H-cycloheptabenzen-5-one (IX) HCl salt, m. 230°, was prepared from 5.5 g. III, 4.8 g. V, and 1.1 g. VI in 37% yield. α-[2-(1-Piperidyl)-ethyl]benzhydrol, m. 109° [HCl salt, m. 238° (from EtOH)] (X), was prepared from BzCH₂CH₂NC₅H₁₀ and PhMgBr. PhMgBr (prepared from 7.8 g. Mg and 49.5 g. PhBr in 30 mL. ether) treated with 35.5 g. VIII and the mixture decomposed with 150 mL. 25% solution of NH₄Cl gave 23 g. (56%) 1,2,4-tetrahydro-1-phenyl-2-(1-piperidylmethyl)-1-naphthol (XI), b_0.5 192-6°, m. 136-7° (from 80% EtOH); HCl salt, m. 23° (decomposition) (from EtOH). 6,7,8,9-Tetrahydro-5-phenyl-6- (1-piperidylmethyl)- 5H-cyclopentabenzen-5-ol (XII), b_0.5 200-5°, m. 144-5°, HCl salt, m. 233-4° (from Me₂CO), was prepared analogously from 3.8 g. Mg, 24 g. PhBr, and 18 g. IX in a 40% yield (8.3 g.). Dehydration of X by boiling with a mixture of HCl and AcOH gave Ph₂C: CHCH₂NC₅H₁₀, b_0.3 158-78°; HCl salt, m. 210-11° (from Me₂CO). VII (29.5 g.) with PhMgBr (prepared from 6.3 g. Mg and 39 g. PhBr in 350 mL. ether) gave directly 14.7 g. (47%) 3-phenyl-2-(1-piperidylmethyl)indene, b_1.2 190-200°, m. 112.5° (from EtOH); HCl salt, m. 233-4° (from EtOH). XI (15 g.) was refluxed 48 h. with 70 mL. HCO₂H at 120-30°, then diluted with 500 mL. H₂O, neutralized with 40% NaOH to pH 5-6, and extracted with ether yielded 11.6 g. (82%) 3,4-dihydro-1-phenyl-2-(1-piperidyl)-methylnaphthalene, b_0.5 178-82°, m. 73.5° (from EtOH); HCl salt (with 1 mol EtOH), m. 188° (from Me₂CO). Similar dehydration of 6.7 g. XII with 35 mL. HCO₂H gave 6.1 g. 8,9-dihydro-5-phenyl-6-(1-piperidyl)methyl-7H-cycloheptabenzene, m. 104.5° (from EtOH); HCl salt, m. 216-18° (from EtOH). Hydrogenation of the unsaturated products was carried out in MeOH solutions over Pd-C catalysts and yielded, resp., Ph₂CHCH₂CH₂NC₅H₁₀ (XlII) (HCl salt, m. 214-16°); 1-phenyl-2-methylindan, b₁ 107-8°; 1,2,3,4-tetra-hydro-2-methyl-1-phenylnaphthalene, b_1.5140 5°, m. 52-3°; and 6,7,8,9-tetrahydro-6-methyl-5-phenyl-5H-cycloheptabenzene, b_0.6 135-8°. XIII was also prepared from NaNH₂ and Ph₂C(CN)CH₂CH₂NC₅H₁₀. 2-Methyl-1(2H)-naphthalenone (XIV), b₂₀ 143-5°, was obtained by cyclization of PhCH₂CH₂CHMeCOCl (XV), with AlCl₃ in a 78% yield. XV was obtained from PhCH₂CH₂CHMeCO₂H, b₂₀ 179-82°, prepared from PhCH₂CH₂CMe(CO₂H)₂, m. 160°, di-Et ester, b_0.4 140-2_° b₃₀ 198-202°. XIV (16 g.) was added to PhMgBr (prepared from 3.2 g. Mg and 20.9 g. PhBr in 100 mL. Et₂O), the mixture decomposed with 30 g. NH₄Cl in 60 mL. H₂O, and extracted with ether; evaporation of the solvent yielded 9 g. (38%) 1,2,3,4-tetrahydro-2-methyl-1-phenyl-1-naphthol (XVI), b_0.9 147-50°, m. 76-7° (from petr. ether). XVI (3 g.) refluxed 48 h. with HCO₂H gave 1.5 g. (54%) 3,4-dihydro-2-methyl-1-phenylnaphthalene, b_0.5 123-4°. The same product, b_0.5 130-5°, was obtained by hydrogenolysis of 3,4-dihyro-1-phenyl-2-(1-piperidylmethyl)naphthalene when the reaction was interrupted after consumption of 2 equivalents

Chemicke Listy pro Vedu a Prumysl published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Computed Properties of 1949-41-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia