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Acetic Acid → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(1-oxoisoindolin-2-yl)piperidino]butyl]-N-methylbenzamide hydrochloride

HRID 1601149
ノート
印刷プレビュー

反応式

HRID 1601149 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:21][CH:22]=O)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:24]=[C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][N:26]1[CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(=O)(O)[O-].[Na+]>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:21][CH2:22][N:37]2[CH2:38][CH2:39][CH:34]([N:26]3[CH2:27][C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:25]3=[O:24])[CH2:35][CH2:36]2)[CH2:10][N:11]([CH3:20])[C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 15381108(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamideHCID 154319612-(Piperidin-4-yl)isoindolin-1-one

生成物 1

HCID 67586095(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(1-oxoisoindolin-2-yl)piperidino]butyl]-N-methylbenzamide hydrochloride収率 172.4%

試薬・触媒・溶媒

2
HCID 887Methanol溶媒3 回HCID 516892Sodium Bicarbonate溶媒

実験手順

(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide (270 mg) in methanol (2 mL) was added to a solution of 4-(1-oxoiso-indolin-2-yl)piperidine (200 mg) and acetic acid (0.053 mL) in methanol (3 mL). After 15 minutes, sodium cyanoborohydride (58 mg) in methanol (1 mL) was added in a single portion. After 6 hours, the reaction mixture was diluted with aqueous sodium bicarbonate, stirred for 30 minutes, and extracted with dichloromethane. The organic extracts were dried, evaporated, and chromatographed, with dichloromethane:methanol (gradient 98:2, 95:5) as the eluent. The resulting material was dissolved in dichloromethane, precipitated out as the hydrochloride salt with ethereal hydrogen chloride, evaporated, and placed under high vacuum overnight to give the title compound (390 mg) as a white solid; MS: m/z=550(M+1). Analysis for C31H33Cl2N3O2 ·1.65 HCl·0.40 (CH3CH2O): Calculated: C, 61.14; H, 6.08; N, 6.56; Found: C, 61.09; H, 6.10; N, 6.48.

後処理

  1. waitAfter 6 hours
  2. extractionextracted with dichloromethane
  3. customThe organic extracts were dried
  4. customevaporated
  5. customchromatographed, with dichloromethane
  6. dissolutionThe resulting material was dissolved in dichloromethane
  7. customprecipitated out as the hydrochloride salt with ethereal hydrogen chloride
  8. customevaporated
  9. customplaced under high vacuum overnight

出典と根拠

ORDレコード
ord-f8f72e5bdca5406fa3edb6e085804663
出典データセット
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05977135

反応ノート

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