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

HRID 83979

反応式

HRID 83979 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-ca98a52b02d141e9a3692979e8c3ee85
出典データセット
uspto-grants-2014_09
特許番号
US08846907B2

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