Benzyl Chloride → (1-Benzylpiperidin-2-yl)methanol

HRID 544256Notes

Reaction equation

HRID 544256 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].[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:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 94263Piperidin-2-ylmethanol

Product 1

HCID 2735486(1-Benzylpiperidin-2-yl)methanolYield 52.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 12.9 g of 2-piperidine methanol, 13.2 g of benzyl chloride, 10.5 g of triethylamine and 50 ml of toluene was stirred at reflux for 4 hours. The reaction mixture was filtered, the filtrate was concentrated, and the concentrate was distilled under reduced pressure to obtain 11.3 g of 1-benzyl-2-piperidine methanol (yield: 52.9%). b.p.: 107° C./2 mmHg

Workup

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

Sources & evidence

ORD record
ord-c67be1fa375245748babc16a131bb96c
Source dataset
uspto-grants-1984_05
Patent number
US04448964

Reaction notes

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