Water → trans-(-)-4-(4-Fluorophenyl)-3-hydroxymethylpiperidine monohydrate

HRID 1016676Notes

Reaction equation

HRID 1016676 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]2[CH2:14][OH:15])=[CH:4][CH:3]=1.O>C1(C)C=CC=CC=1>[OH2:15].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]2[CH2:14][OH:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 9855829(3S,4R)-4-(4-Fluorophenyl)-3-piperidinemethanol

Product 1

HCID 69039254trans-(-)-4-(4-Fluorophenyl)-3-hydroxymethylpiperidine monohydrateYield 89.45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 200-ml four-necked glass flask equipped with a thermometer and a reflux condenser was charged with 63 ml of toluene and 10.54 g (50.37 mmol) of (−)-(3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine, and the mixture was warmed and dissolved. 1.13 g (62.71 mmol) of water was added to the above mixture at 50° C. to allow to crystallize. Thereafter, the mixture was kept for one hour at a temperature of from 20° to 30° C., and then the crystals were collected by filtration. The obtained crystals were thoroughly washed with 20 ml of toluene, to give white crystals of (−)-(3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine monohydrate. Thereafter, the crystals were dried under a reduced pressure at a temperature of 30° C. or lower, and weighed 10.24 g. The yield was 89.45% based on (−)-(3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine.

Workup

  1. customA 200-ml four-necked glass flask equipped with a thermometer and a reflux condenser
  2. temperaturethe mixture was warmed
  3. dissolutiondissolved
  4. customto crystallize
  5. filtrationthe crystals were collected by filtration
  6. washThe obtained crystals were thoroughly washed with 20 ml of toluene

Sources & evidence

ORD record
ord-8e4e9f87089c46f1b9f46d2e3df1680d
Source dataset
uspto-grants-2002_11
Patent number
US06476227B1

Reaction notes

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