Phenethyl bromide → HCID 57321464, compound

HRID 1447807Notes

Reaction equation

HRID 1447807 reaction equation
[CH2:1](Br)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([O:12][C:13](=[O:23])[CH:14]([C:16]1(O)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:15])[CH3:11].[C:24](=[O:27])([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:10]([O:12][C:13](=[O:23])[CH:14]([CH:16]1[CH2:21][CH2:20][N:19]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:18]([C:24]2([OH:27])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:17]1)[CH3:15])[CH3:11]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium Carbonate2×HCID 54216309HCID 54216309, compound

Product 1

HCID 57321464HCID 57321464, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 12.0 g of phenethyl bromide in 50 cc of dimethyl formamide is added dropwise at a temperature of 60°, with stirring, to a suspension of 18.9 g of crude 2-(4-hydroxy-4-piperidyl)propionic acid ethyl ester and 11.5 g of potassium carbonate in 150 cc of dimethyl formamide. The reaction mixture is stirred at 60° for a further 11/2 hours, is then poured in a 10% potassium carbonate solution containing ice and extraction is effected with ether. The title compound, obtained after drying the ether extracts over magnesium sulphate and concentrating by evaporation, is dissolved in acetone, the calculated amount of maleic acid is added, and the resulting crude hydrogen maleate is repeatedly recrystallized from acetone. The hydrogen maleate form of the title compound has a M.P. of 138°-139°.

Workup

  1. additioncontaining
  2. extractionice and extraction

Sources & evidence

ORD record
ord-e402b0fcfce2455097b22140b940ccf7
Source dataset
uspto-grants-1979_12
Patent number
US04178377

Reaction notes

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