DeBenneville, Peter L. published the artcileBehavior of aliphatic aldehydes in the Leuckart-Wallach reaction, Application of 2-Ethyl-N,N-dimethylhexan-1-amine, the publication is Journal of the American Chemical Society (1950), 3073-5, database is CAplus.
The Leuckart-Wallach reaction with aliphatic aldehydes and secondary amines is initiated at a generally lower temperature than in the case of ketones and aromatic aldehydes and generally gives good yields of products. A possible explanation is the involvement of the H on the ¦Á-C atom of the aldehyde through an enamine intermediate. The following compounds were used: Aldehydes, EtCHO (I), PrCHO (II), iso-PrCHO (III), C6H13CHO (IV), BuEtCHCHO (V), Me3CCH2CHMeCH2CHO (VI); ketones, cyclohexanone (VII), PhAc (VIII); amines, morpholine (IX), piperidine (X), Me2NH (XI), (iso-Pr)2NH (XII), (HOC2H4)2NH (XIII), MeNHC9H19 (XIV), and PhNHMe (XV). The enamines were prepared by the method of Mannich and Davidsen (C.A. 30, 8217.2), with anhydrous K2CO3 or CaO as catalyst and temperatures of 5-50¡ã; the intermediate diimine was converted to the enamine by distillation One mol. of the enamine is treated dropwise with 1-1.1 mols. 98% HCO2H, heated 1-2 h. at 50-70¡ã (occasionally at 90¡ã), poured into dilute HCl, extracted with ether, made basic with NaOH, and again extracted with ether. Enamines, Satd amine; Aldehyde, Amine, Yield, %, B.p., ¡ãC., Mm., Yield, %, B.p., ¡ãC., Mm.; II, IX, 95, 105-10, 20, 54, 94-9, 25; III, IX, 29, 89-93, 20, 73, 80-5, 20; IV, IX, 76, 91-4, 2, 32, 90-5, 2; IV, X, 60, 111-12, 3, 84, 78-82, 1; V, IX, 41, 95-115, 1, 60, 81, 0.7; VI, XI, 42, 46-50, 1, 80, 46, 1.5; VI, XII, 23, 79-81, 2, 62, 98-100, 4; VI, IX, 79, 107-10, 3, 85, 81-3, 2; VI, XIII, 52, 105-10, 0.7, 84, 147-50, 1.3; VI, XIV, 70, 117-21, 1, 57, 124-33, 1.5; In carrying out the Leuckart-Wallach alkylations, 1 mol. of the amine was added to 1 mol. HCO2H, the temperature raised to 60¡ã, and the aldehyde added dropwise (1 h.); the mixture was then heated about 1 h. on. the steam bath; for I and II, the amine-HCO2H ratio was 1:2. The following reactions are reported: Aldehyde, Amine, Yield, %, B.p., ¡ãC., Mm.; I, IX, 5, 78-82, 35; II, XI, 60, 94-6, 760; II, IX, 34, 95-8, 22; III, XI, 59, 70-6, 760; III, IX, 57, 80-4, 15; IV, IX, 46, 76-87, 1; V, XI, 60, 88-90, 20; VI, XI, 84, 52-5, 3; VI, XII, 47, 85-8, 2; VI, XIV, 54, 115-21, 1.5; VI, XV, 17, 117-40, 1.7; VII, X, 25, 113-15, 18; VIII, X, 0, -, -;
Journal of the American Chemical Society published new progress about 28056-87-3. 28056-87-3 belongs to catalysis-chemistry, auxiliary class Amine,Aliphatic hydrocarbon chain, name is 2-Ethyl-N,N-dimethylhexan-1-amine, and the molecular formula is C10H23N, Application of 2-Ethyl-N,N-dimethylhexan-1-amine.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia