1-(3-bromophenyl)-N,N-dimethylmethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Bromo-N,N-dimethylbenzylamine (21.4 g) was reacted with magnesium turnings (2.4 g) in dry tetrahydrofuran (75 ml). The mixture was cooled to 0° and gaseous formaldehyde (generated by heating 15 g paraformaldehyde in a stream of argon) was passed over the stirred solution. Tetrahydrofuran (25 ml) was added and the mixture was stirred at room temperature for 2.5 hours and acidified to pH 1. The mixture was extracted with aqueous 3N hydrochloric acid, and the aqueous extracts were made alkaline with aqueous sodium hydroxide and extracted with ether. The ether extracts were evaporated to give 3-(dimethylaminomethyl)benzyl alcohol (14.78 g, 78%). The mixture was cooled to 0° The mixture was extracted with aqueous 3N hydrochloric acid extracted with ether The ether extracts were evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dimethylamine (51.4 g, 1.14 mol) was reacted with 3-bromobenzyl bromide (95 g, 0.38 mol) in benzene at 5° and the mixtue was acidified with hydrochloric acid and the mixture was extracted with aqueous 3N hydrochloric acid. The aqueous extracts were made alkaline with aqueous potassium hydroxide and the oil which separated out was distilled to give 3-bromo-N,N-dimethylbenzylamine (65 g, 80%) b.p. 118°/20 mmHg. the mixture was extracted with aqueous 3N hydrochloric acid the oil which separated out was distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (3-bromo-benzyl)-dimethyl-amine (1.10 g), ethyl acrylate (0.8 ml; 7.7 mmol), tri-o-tolyl-phosphane (156 mg; 0.53 mmol), Pd(OAc)2 (40 mg; 0.16 mmol) and NEt3 (1.4 ml; 10 mmol) is heated under reflux for 8 h. The reaction mixture is evaporated and the residue is subjected to flash chromatography on silica gel eluting with CH2Cl2/MeOH (95:5) to give the compound (800 mg). is heated under reflux for 8 h The reaction mixture is evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (3-bromo-benzyl)-dimethyl-amine (1.10 g), ethyl acrylate (0.8 ml; 7.7 mmol), tri-o-tolyl-phosphane (156 mg; 0.53 mmol), Pd(OAc)2 (40 mg; 0.16 mmol) and NEt3 (1.4 ml; 10 mmol) is heated under reflux for 8 h. The reaction mixture is evaporated and the residue is subjected to flash chromatography on silica gel eluting with CH2Cl2/MeOH (95:5) to give the compound (800 mg). is heated under reflux for 8 h The reaction mixture is evaporated