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

HRID 1489192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1489192
[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]

Komponenten

7

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel3×

Versuchsvorschrift

(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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-70c08587d95e4280b434351e3da6022a
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677317

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