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

HRID 1901385Notes

Reaction equation

HRID 1901385 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 516892Sodium BicarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6e675db8f3ab41ceb9c781b88ec49a62
Source dataset
uspto-grants-1996_11
Patent number
US05576333

Reaction notes

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