Benzyl Chloride → Hydrochloric Acid

HRID 2397910Notes

Reaction equation

HRID 2397910 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 two 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 two hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a79895be10964937b7258b2841d0bd37
Source dataset
uspto-grants-1977_05
Patent number
US04022792

Reaction notes

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