Benzyl Chloride → 1-Benzylpiperidin-3-ol

HRID 544254Notes

Reaction equation

HRID 544254 reaction equation
Cl.[OH:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:9]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([OH:2])[CH2:4]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 2723962Piperidine-3-ol hydrochloride

Product 1

HCID 857731-Benzylpiperidin-3-olYield 56.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 15.0 g of 3-hydroxypiperidine hydrochloride, 13.8 g of benzyl chloride, 22.1 g of triethylamine and 120 ml of toluene was stirred at reflux for 4 hours. The reaction mixture was filtered, and the filtrate was concentrated and distilled under reduced pressure to obtain 11.8 g of 1-benzyl-3-hydroxypiperidine (yield: 56.9%). b.p.: 125°-126° C./3.5 mmHg

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-4a4ba222e85146b9a3e0990b3198c195
Source dataset
uspto-grants-1984_05
Patent number
US04448964

Reaction notes

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