Hydrochloric Acid → 2-(beta-[2-Dimethylaminoethyl]phenethyl)benzoic acid ethyl ester

HRID 1731202Notes

Reaction equation

HRID 1731202 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][CH:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].Cl.[CH2:24](O)[CH3:25]>>[CH2:24]([O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=1[CH2:6][CH:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:25]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 20359294HCID 20359294, compound

Product 1

HCID 539227562-(beta-[2-Dimethylaminoethyl]phenethyl)benzoic acid ethyl ester

Procedure

A solution of 29.7 g. (0.1 mole) of 2-(β-[2-dimethylaminoethyl]phenethyl)benzoic acid in 200 ml. of ethanol is saturated with gaseous hydrochloride, and the resulting mixture is refluxed for 18 hours. The solvent is removed in vacuo and the residue is partitioned between ether and 2N sodium hydroxide. The ether extract is dried and evaporated in vacuo to give 2-(β-[2-dimethylaminoethyl]phenethyl)benzoic acid ethyl ester.

Workup

  1. temperaturethe resulting mixture is refluxed for 18 hours
  2. customThe solvent is removed in vacuo
  3. customthe residue is partitioned between ether and 2N sodium hydroxide
  4. extractionThe ether extract
  5. customis dried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c77498e59f0b48afa89c4ac5a2b92de3
Source dataset
uspto-grants-1976_11
Patent number
US03994961

Reaction notes

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