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Ammonium Hydroxide → 2-(N'-n-butylureido)-5-methylsulfinyl-N-[(1-diphenylmethylpiperidin-4yl)methyl]benzamide

HRID 362938
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 362938
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH:32][C:33]([NH:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:34])=[C:7]([CH:31]=1)[C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:9].[OH:40]OS([O-])=O.[K+].[NH4+].[OH-]>CC#N.C(Cl)Cl.CO.O.C(Cl)Cl>[CH2:36]([NH:35][C:33](=[O:34])[NH:32][C:6]1[CH:5]=[CH:4][C:3]([S:2]([CH3:1])=[O:40])=[CH:31][C:7]=1[C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:14][CH2:13]1)=[O:9])[CH2:37][CH2:38][CH3:39]
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Komponenten

6

Edukt 3

HCID 14923Ammonium HydroxideHCID 23707502Potassium hydroxy sulfite2×HCID 675956385-methylthio-2-(N'-n-butylureido)-N-[(1-diphenylme-thylpiperidin-4-yl)methyl]benzamide

Produkt 1

HCID 675954132-(N'-n-butylureido)-5-methylsulfinyl-N-[(1-diphenylmethylpiperidin-4yl)methyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 86753736HCID 86753736, VerbindungLösungsmittel

Versuchsvorschrift

A solution of 5-methylthio-2-(N'-n-butylureido)-N-[(1-diphenylme-thylpiperidin-4-yl)methyl]benzamide (EXAMPLE 73) (200 mg, 0.367 mmol) in CH3CN/CH2Cl2 /MeOH/H2O (10 ml/2 ml/4 ml/0.5 ml) was agitated with OXONE® (2KHSO5KHSO4K2SO4) (142 mg, 0.231 mmol) for 2 hours at room temperature and then an additional OXONE® (15 mg) was added. The reaction mixture was made basic with 25% NH4OH and diluted with CH2Cl2. The organic layer was washed twice with H2O, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel to give 2-(N'-n-butylureido)-5-methylsulfinyl-N-[(1-diphenylmethylpiperidin-4yl)methyl]benzamide. 130 mg (63%): mp 209°-211° C.; 1H NMR (CDCl3) ppm: 0.91 (3H, t), 1.33-1.88 (11H, m), 2.69 (3H, s), 2.88 (2H, m), 3.22-3.31 (4H, m), 4.24 (1H, s), 4.85 (1H, bt), 7.03 (1H, bt), 7.13-7.42 (11H, m), 7.91 (1H, d), 8.63 (1H, d), 10.71 (1H, s); and 2-(N'-n-butylureido)-5-methylsulfonyl-N-[(1-diphenylmethylpiperidin-4-yl)-methyl]benzamide, 30 mg (14%): mp 178°-179° C.; 1H NMR (CDCl3) ppm: 0.93(3H, t), 1.31-1.88 (11H, m), 2.90 (2.90 (2H, m), 3.02 (3H, s), 3.23-3.34 (4H, m), 4.25 (1H, s), 4.79 (1H, bt), 6.61 (1H, bt), 7.13-7.40 (10H, m), 7.89 (1H, dd), 7.97 (1H, d), 8.73 (1H, d), 10.82 (1H, s), respectively.

Aufarbeitung

  1. washThe organic layer was washed twice with H2O
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8fd449b5d86f4c1c8b58d9037c8142e3
Quelldatensatz
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05872115

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