Glycine → N-[(4-Bromophenyl)methyl]glycine

Participants

Reaction Steps

To a solution of glycine (8.11 g, 108 mmol) in water (40 ml) were added an aqueous solution of sodium hydroxide (108 mmol, 15 ml) and a solution of 4-bromobenzaldehyde (20 g, 108 mmol) in methanol (240 ml). After 30 minutes stirring at room temperature sodium borohydride (4.09 g, 108 mmol) was added portionwise to this suspension. After 18 h stirring at room temperature the reaction mixture was concentrated under reduced pressure and the resulting aqueous phase was washed with diethyl ether. The aqueous phase was neutralized by the addition of an aqueous solution of 2M hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and diethyl ether. Drying the white solid afforded 2-(4-bromobenzylamino)acetic acid (14.2 g). The product was used in the following step without further purification.

Provenance & Evidence