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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1601149
[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]
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Komponenten

7

Edukt 4

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

Produkt 1

HCID 67586095(S)-N-[2-(3,4-Dichlorophenyl)-4-[4-(1-oxoisoindolin-2-yl)piperidino]butyl]-N-methylbenzamide hydrochlorideAusbeute 172,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel3×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

(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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f8f72e5bdca5406fa3edb6e085804663
Quelldatensatz
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05977135

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