Acetic Acid → (S)-N-[2-(3,4-Dichlorophenyl)-4-[4-ethoxycarbonyl-4-(2-oxopiperidino) piperidino]butyl]-N-methylbenzamide hydrochloride

HRID 1489192Notes

Reaction equation

HRID 1489192 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].C(O[C:27]1([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][C:36]2=[O:41])[CH2:32][CH2:31][NH:30][C:29](=C=O)[CH2:28]1)C.[C:42](O)(=O)[CH3:43].C([BH3-])#N.[Na+].[C:50](=[O:53])(O)[O-:51].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:21][CH2:22][N:30]2[CH2:29][CH2:28][C:27]([C:50]([O:51][CH2:42][CH3:43])=[O:53])([N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][C:36]3=[O:41])[CH2:32][CH2:31]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 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 15381108(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamideHCID 867496274-Ethoxy-carbonyl-4-(2-oxopiperidino)piperidine

Product 1

HCID 22878239(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-ethoxycarbonyl-4-(2-oxopiperidino) piperidino]butyl]-N-methylbenzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

(S)-N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide (415 mg) in methanol (3 mL) was added to a solution of 4-ethoxy-carbonyl-4-(2-oxopiperidino)piperidine (391 mg) and acetic acid (0.09 mL) in methanol (6 mL). After 15 minutes, sodium cyanoborohydride (100 mg) in methanol (3 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 (95:5) as 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 as a white solid (630 mg); MS: m/z=588(M+1). Analysis for C31H39Cl2N3O4 ·1.70 HCl·0.20 (C2H5)2O: Calculated: C, 57.40; H, 6.46; N, 6.31; Found: C, 57.40; H, 6.37; N, 6.17.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with dichloromethane
  3. customThe organic extracts were dried
  4. customevaporated
  5. customchromatographed, with dichloromethane:methanol (95:5) as eluent
  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-70c08587d95e4280b434351e3da6022a
Source dataset
uspto-grants-1997_10
Patent number
US05677317

Reaction notes

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