N-(2-phenylethyl)acetamide → Methyl 5-oxo-5-[4-(2-acetaminoethyl)-phenyl]-pentanoate

HRID 2248136Notes

Reaction equation

[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[Cl-].[CH3:14][O:15][C:16](=[O:23])[CH2:17][CH2:18][CH2:19][C:20](O)=[O:21].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[O:21]=[C:20]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][NH:4][C:1]([CH3:2])=[O:3])=[CH:8][CH:9]=1)[CH2:19][CH2:18][CH2:17][C:16]([O:15][CH3:14])=[O:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 26.9 g. (0.165 mol) acetylphenethylamine (preparation see J. Am. Pharm. Assoc., 47, 353/1958) in 300 ml. methylene chloride is added dropwise first 30.0 g. (0.182 mol) glutaric acid methyl ester chloride and then 66.1 g. (0.495 mol) aluminium chloride are added portionwise thereto at 0° to 5° C. The reaction mixture is further stirred for 1 hour at 0° C., then allowed to warm up to ambient temperature and after 4 hours the reaction mixture is poured on to ice/hydrochloric acid. The organic phase is separated off, washed neutral with water and dried over anhydrous sodium sulphate. After stripping off the solvent, there are obtained 34 g. (71% of theory) of colourless crystals; m.p. 107°-108° C., after recrystallisation from ethyl acetate.

Workup

customat 0° to 5° C
temperatureto warm up to ambient temperature and after 4 hours the reaction mixture
customThe organic phase is separated off
washwashed neutral with water
dry with materialdried over anhydrous sodium sulphate
customare obtained 34 g
customm.p. 107°-108° C., after recrystallisation from ethyl acetate

Sources & evidence

ORD record: ord-5ee0bd105baa4130afb4df5c824aac02
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05037990

Reaction notes

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