Diisopropylethylamine → 1-(trans-3-(4-Chlorophenyl)allyl)-perhydroazepin-4-one

HRID 2068500Notes

Reaction equation

HRID 2068500 reaction equation
Cl.[NH:2]1[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[Cl:19][C:20]1[CH:29]=[CH:28][C:23]([CH:24]=[CH:25][CH2:26]Cl)=[CH:22][CH:21]=1>C(#N)C>[Cl:19][C:20]1[CH:29]=[CH:28][C:23](/[CH:24]=[CH:25]/[CH2:26][N:2]2[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH2:4][CH2:3]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22021728Azepan-4-one hydrochlorideHCID 53728250p-Chlorocinnamyl chloride

Product 1

HCID 689273051-(trans-3-(4-Chlorophenyl)allyl)-perhydroazepin-4-oneYield 48.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Perhydroazepinone hydrochloride (2.5 g, prepared according to Synth. Commun. 1992, 1249-1258) was suspended in acetonitrile (80 ml); diisopropylethylamine (4.4 ml) and 4-chlorocinnamyl chloride (2.7 g) were successively added at room temperature and the resulting reaction mixture was stirred at room temperature for 20 hours. The solvent was removed in vacuo and the residue purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4) to afford 1-(trans-3-(4-chlorophenyl)allyl)-perhydroazepin-4-one (1.84 g) as a foam. MS (ES+) 264/266 (M+H+).

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4)

Sources & evidence

ORD record
ord-240382e3c47348309f74c6c1d6cf5ed0
Source dataset
uspto-grants-2012_10
Patent number
US08299058B2

Reaction notes

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