Dimethyl Sulfoxide → HCID 21514117, compound

HRID 1576117Notes

Reaction equation

HRID 1576117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:27])[CH2:13][CH2:12][N:11]([CH:14](F)[CH2:15][CH:16]([F:25])[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2([OH:41])[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[CH:31][CH:30]=1.CS(C)=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:27])[CH2:13][CH2:12][N:11]([CH:14]([N:38]3[CH2:37][CH2:36][C:35]([OH:41])([C:32]4[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=4)[CH2:40][CH2:39]3)[CH2:15][CH:16]([F:25])[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 21514083HCID 21514083, compound

Product 1

HCID 21514117HCID 21514117, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of γ-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,4-difluorobutyrophenone (3.94 g), 4-(p-chlorophenyl)-4-hydroxypiperidine (2.24 g) and dimethylsulfoxide (30 ml) was stirred at room temperature for 14 hours. The mixture was poured into 300 ml of water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethanol to yield γ,4-bis-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2-fluorobutyrophenone. M.P. 190° - 193°C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8aa85a45f2bb49e292eed2df293ebffe
Source dataset
uspto-grants-1976_09
Patent number
US03979390

Reaction notes

Loading…