N-(2-phenylethyl)acetamide → Methyl 4-oxo-4-{4-[2-(N-acetylamino)-ethyl]-phenyl}-butyrate

HRID 2248133Notes

Reaction equation

HRID 2248133 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:7])[CH3:6].[Cl-].[CH3:18][O:19][C:20](=[O:26])[CH2:21][CH2:22][C:23](O)=[O:24]>C(Cl)Cl>[O:24]=[C:23]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][NH:8][C:5](=[O:7])[CH3:6])=[CH:12][CH:13]=1)[CH2:22][CH2:21][C:20]([O:19][CH3:18])=[O:26]

Participants

5

Reactant 3

HCID 70143N-(2-phenylethyl)acetamideHCID 6451240Aluminum(III) ChlorideHCID 86605420Succinic acid methylester chloride

Product 1

HCID 19805569Methyl 4-oxo-4-{4-[2-(N-acetylamino)-ethyl]-phenyl}-butyrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

272.7 g. (2.04 mol) aluminium chloride are introduced portionwise at 0° C. into a solution of 110.97 g. (0.68 mol) N-acetylphenethylamine and 93 ml. (0.75 mol) succinic acid methyl ester chloride in 1200 ml. anhydrous methylene chloride, the reaction mixture is further stirred for 1 hour at 0° C. and then warmed to ambient temperature. The reaction mixture is poured into hydrochloric acid/ice water, the organic phase is separated off, dried over anhydrous magnesium sulphate and evaporated. The residue is stirred up with hot diethyl ether, filtered off with suction and afterwashed with a little cold diethyl ether. Yield 154 g. (82% of theory); colourless crystals; m.p. 119.5° C.

Workup

  1. customthe organic phase is separated off
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customevaporated
  4. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-e98d408418fb45e788decd7f00a515f4
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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