Oxalyl chloride → 1-Benzylpiperidine-4-carbonyl chloride

HRID 1291187Notes

Reaction equation

HRID 1291187 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:20])=O>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([Cl:20])=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 65578Oxalyl chlorideHCID 47149831-Benzylpiperidine-4-carboxylic acid

Product 1

HCID 189197671-Benzylpiperidine-4-carbonyl chlorideYield 99%

Procedure

0.33 g (0.0015 mol) of 1-benzylpiperidine-4-carboxylic acid was dissolved in 5 ml of oxalyl chloride for 2 hrs. The excess oxalyl chloride was distilled off. The residue was taken up twice in toluene and concentrated each time. 0.355 g (99%) of 1-benzyl-piperidine-4-carboxylic acid chloride was obtained as a pale beige solid. This was dissolved in 20 ml of toluene, treated with 0.3 ml (0.00224 mol) of triethylamine and 0.184 g (0.00195 mol) of phenol and boiled at reflux for 18 hrs. After removal of the solvent the residue was chromatographed on silica gel with ether/hexane (1:2.5→1:2) as the eluent. 0.315 g (71%) of phenyl 1-benzyl-piperidin-4-carboxylate was obtained as a yellow oil. MS: me/e=296 (C9H22NO2+).

Workup

  1. distillationThe excess oxalyl chloride was distilled off
  2. concentrationconcentrated each time

Sources & evidence

ORD record
ord-f55f13189c6a403a9ef51a0b614b563d
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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