Benzyl Chloride → Hydrochloric Acid

HRID 1283982Notes

Reaction equation

HRID 1283982 reaction equation
Br.[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C@H:9]2[C@@H:14]([C:15]([OH:17])=[O:16])[CH2:13][CH2:12][CH2:11][NH:10]2)=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+].[CH2:25]([Cl:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[ClH:32].[CH2:25]([N:10]1[CH2:11][CH2:12][CH2:13][C@H:14]([C:15]([OH:17])=[O:16])[C@@H:9]1[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:19][CH:18]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 516892Sodium BicarbonateHCID 68125015HCID 68125015, compound

Product 2

HCID 313Hydrochloric AcidHCID 68125536HCID 68125536, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9.9 g. of cis-2-(p-methoxybenzyl)-3-piperidinecarboxylic acid hydrobromide, 7.6 g. of sodium bicarbonate, 3.8 g. of benzyl chloride, and 100 ml. of dimethylformamide is stirred and refluxed for 2 hours. The reaction mixture is concentrated under reduced pressure, and the resulting residue is taken up in 100 ml. of water. By acidification with 30 ml. of N hydrochloric acid, there is produced cis-1-benzyl-2-(p-methoxybenzyl)-3-piperidinecarboxylic acid.

Workup

  1. additionA mixture of 9.9 g
  2. temperaturerefluxed for 2 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-0bf86287628e412ea86290a9adf14ef1
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

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