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

HRID 744895ノート

反応式

HRID 744895 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH: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[CH2:29][CH2:28][CH2:27][N:26]1[CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]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]([CH:9]([CH2:21][CH2:22][N:33]2[CH2:32][CH2:31][CH:30]([N:26]3[CH2:27][CH2:28][CH2:29][C:25]3=[O:24])[CH2:35][CH2:34]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

7

反応物 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 183142501-(Piperidin-4-yl)pyrrolidin-2-oneHCID 22137499N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide

生成物 1

HCID 23369936N-[2-(3,4-Dichlorophenyl)-4-[4-(2-oxopyrrolidin-1-yl)-piperidino]butyl]-N-methylbenzamide hydrochloride収率 149.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒3 回HCID 516892Sodium Bicarbonate溶媒

実験手順

N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide (870 mg) in methanol (2.4 mL) was added to a solution of 4-(2-oxopyrrolidin-1-yl)piperidine (0.460 g) and acetic acid (0.16 mL) in methanol (2.4 mL). After 5 minutes, sodium cyanoborohydride (0.173 g) in methanol (2.4 mL) was added in a single portion. After being stirred for 3 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, 90:10) 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 (1.0 g) as a white solid; MS: m/z=502(M+1). Analysis for C27H33Cl2N3O2.1.50 HCl: Calculated: C, 58.20; H, 6.24; N, 7.54; Found: C, 58.18; H, 6.27; N, 7.44.

後処理

  1. stirringstirred for 30 minutes
  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-9b1b9b3325434db1b2eba081d10857e2
出典データセット
uspto-grants-1996_09
特許番号
US05559131

反応ノート

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