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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
Notes
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Reaction equation

HRID 1601149 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 516892Sodium BicarbonateSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-f8f72e5bdca5406fa3edb6e085804663
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05977135

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes