Cyclohexanecarboxaldehyde → HCID 51032206, compound

HRID 1931533Notes

Reaction equation

C1(C(C2C=CC=CC=2)(CC=C)CN)C=CC=CC=1.C1(C=O)CCCCC1.[CH2:27]([NH:34][CH2:35][C:36]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:37][CH:38]=[CH2:39])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH:28]1([CH2:27][NH:34][CH2:35][C:36]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:37][CH:38]=[CH2:39])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

Reactant 3

HCID 16275Cyclohexanecarboxaldehyde

HCID 11402147HCID 11402147, compound

HCID 24885922HCID 24885922, compound

Product 1

HCID 51032206HCID 51032206, compoundYield 97%

Procedure

N-(Cyclohexylmethyl)-2,2-diphenylpent-4-en-1-amine was prepared from 2,2-diphenylpent-4-enylamine and cyclohexanecarboxaldehyde according to the procedure used for preparation of N-benzyl-2,2-diphenylpent-4-en-1-amine. The product was obtained in a 97% yield as a colorless oil. The compound was purified by column chromatography on silica gel (Hexane/Ethyl acetate=8/1). 1H NMR (400 MHz, CDCl3) δ 0.41 (s, 1H), 0.74-0.83 (m, 2H), 1.08-1.41 (m, 4H), 1.59-1.71 (m, 5H), 2.38 (d, J=6.8 Hz, 2H), 3.05 (d, J=6.8 Hz, 2H), 3.20 (s, 2H), 4.97 (dt, J=10.4, 0.12 Hz, 1H), 5.06 (dt, J=16.8, 1.2 Hz, 1H), 5.36-5.47 (m, 1H), 7.19-7.33 (m, 10H); 13C NMR (100 MHz, CDCl3) δ 26.3, 27.1, 31.6, 37.7, 41.9, 50.4, 56.3, 57.5, 117.8, 126.1, 128.2, 123.3, 135.3, 147.3.

Workup

customThe product was obtained in a 97% yield as a colorless oil
customThe compound was purified by column chromatography on silica gel (Hexane/Ethyl acetate=8/1)

Sources & evidence

ORD record: ord-24ef7ed6c862426bb5b995d68e907680
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188302B2

Reaction notes

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