Dimethylformamide → 4-(4-Chlorophenyl)-1-[3-(4-fluorophenoxy)propyl]-4-piperidinol

HRID 1658514Notes

Reaction equation

HRID 1658514 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([OH:26])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[F:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:23]2[CH2:22][CH2:21][C:20]([C:17]3[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=3)([OH:26])[CH2:25][CH2:24]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 743911-(3-Chloropropoxy)-4-fluorobenzene

Product 1

HCID 215277714-(4-Chlorophenyl)-1-[3-(4-fluorophenoxy)propyl]-4-piperidinol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.83 g of 1-chloro-3-(p-fluorophenoxy)-propane, 3.18 g of 4-(p-chlorophenyl)-4-hydroxypiperidine, 0.8 g of sodium carbonate and 60 ml of dimethylformamide is heated at a temperature of 80° - 90°C for 10 hours. After cooling, the reaction mixture is poured into water. The precipitate is collected by filtration and dried to give 1-[3-(p-fluorophenoxy)-propyl]-4-(p-chlorophenyl)-4-hydroxypiperidine, M.P. 134 - 135°C. Recrystallization from benzene gives the purified product, M.P. 136° - 137°C.

Workup

  1. temperatureis heated at a temperature of 80° - 90°C for 10 hours
  2. temperatureAfter cooling
  3. filtrationThe precipitate is collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-3ac06d4e711343d0a7a941858b0ae3bf
Source dataset
uspto-grants-1976_06
Patent number
US03965106

Reaction notes

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