Dimethyl Sulfoxide → HCID 21514174, compound

HRID 1576113Notes

Reaction equation

HRID 1576113 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:28])[CH2:14][CH2:13][N:12]([CH:15](F)[CH2:16][CH:17]([F:26])[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CS(C)=O>O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:28])[CH2:14][CH2:13][N:12]([CH:15]([NH:36][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:16][CH:17]([F:26])[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7504BenzylamineHCID 21514082HCID 21514082, compound

Product 1

HCID 21514174HCID 21514174, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of γ-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,4-difluorobutyrophenone hydrochloride (4.0 g), benzylamine (20.0 g) and dimethylsulfoxide (100 ml) was stirred at 70° to 80°C for 8 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was sufficiently washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Treatment of the residue with ethanol afforded γ-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-4-benzylamino-2-fluorobutyrophenone. M.P. 158° - 165°C. IR νmaxNujol 3350, 1650 cm-1.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was sufficiently washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-49d94b75aa60440a9fd8028cc10ae2e4
Source dataset
uspto-grants-1976_09
Patent number
US03979390

Reaction notes

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