3,3-Diphenylacrolein → 4-(4-(3,3-Diphenyl-2-propenyl)-1-piperazinyl)benzonitrile

HRID 731544

反応式

HRID 731544 の反応式
Cl.[N:2]1([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:16]1([C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:23][CH:24]=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.C([BH3-])#N>ClCCl.CO>[C:16]1([C:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:23][CH2:24][N:5]2[CH2:6][CH2:7][N:2]([C:8]3[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=3)[CH2:3][CH2:4]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 710273,3-DiphenylacroleinHCID 81531DiisopropylethylamineHCID 498716Cyano-borohydrideHCID 27339944-(Piperazin-1-yl)benzonitrile hydrochloride

生成物 1

HCID 591866114-(4-(3,3-Diphenyl-2-propenyl)-1-piperazinyl)benzonitrile収率 84.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A suspension of 4-piperazin-1-ylbenzonitrile hydrochloride (1.30 g, 5.00 mmol) and 3,3-diphenylacrylaldehyde (1.56 g, 7.50 mmol)) in dichloromethane (10 mL) and methanol (10 mL) was neutralized to pH 5 with diisopropylethylamine, treated with polymer-supported cyanoborohydride (2.47 mmol/g, 6 g, 14.82 mmol), shaken at room temperature for 24 hours, and filtered. The resin was washed with 1:1 dichloromethane/methanol (10 mL×3) and the combined filtrates were concentrated. The concentrate was purified by silica gel chromatography eluting with a gradient from 10%-50% ethyl acetate/hexanes to provide the desired product (1.60 g, 84%). MS (CI) m/e 380 (M+H)+.

後処理

  1. filtrationfiltered
  2. washThe resin was washed with 1:1 dichloromethane/methanol (10 mL×3)
  3. concentrationthe combined filtrates were concentrated
  4. customThe concentrate was purified by silica gel chromatography
  5. washeluting with a gradient from 10%-50% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-0b4095b6d8be45d7a5f7dc22995109e0
出典データセット
uspto-grants-2009_09
特許番号
US07585858B2

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