Water → 5-(1-Methylethyl)-3-[(1-methylpiperidin-4-yl)sulfonyl]-1H-indole

HRID 36889Notes

Reaction equation

HRID 36889 reaction equation
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[CH3:9][CH:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[S:21][CH:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1)[CH3:11].[OH2:29]>>[CH3:11][CH:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[S:21]([CH:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1)(=[O:2])=[O:29])[CH3:9]

Participants

4

Reactant 3

HCID 962WaterHCID 10313463Potassium peroxymonosulphateHCID 199366285-(1-methylethyl)-3-[(1-methylpiperidin-4-yl)thio]-1H-indole

Product 1

HCID 199366475-(1-Methylethyl)-3-[(1-methylpiperidin-4-yl)sulfonyl]-1H-indole

Procedure

A solution of potassium peroxymonosulfate (49.5% KHSO5, 21.2 g) in water (95 ml) is added drop-wise at 0° C. to a methanolic solution (95 ml) of 5-(1-methylethyl)-3-[(1-methylpiperidin-4-yl)thio]-1H-indole (7.5 g, prepared in Example 43). After 4 hours at room temperature, the white precipitate is filtered off and the filtrate is concentrated, rendered basic with sodium carbonate and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. 5-(1-Methylethyl)-3-[(1-methylpiperidin-4-yl)sulfonyl]-1H-indole (2.4 g) is obtained after purification on silica gel (eluent: CH2Cl2 /iPrNH2 95/5).

Workup

  1. filtrationthe white precipitate is filtered off
  2. concentrationthe filtrate is concentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ffc00cac7a57496b9c1e95ac2274109a
Source dataset
uspto-grants-1995_05
Patent number
US05418242

Reaction notes

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