Hydrochloric Acid → HCID 68983197, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl N-(3-chloro-4-fluorophenyl)valinate (8-1, 0.20 g, 0.74 mmol), benzylbromide (0.380 g, 2.21 mmol), and diisopropylethyleneamine (0.11 g, 0.89 mmol) were combined in DMF (0.1 mL) and stirred 18 h at 50° C. Additional benzylbromide (0.43 g, 2.5 mmol) and diisopropylethylamine (0.22 g, 1.7 mmol) were added and mixture was heated to 60° C. for 4 h and then 50° C. for 18 h. Ethylenediamine (0.266 g, 4.43 mmol) and CH2Cl2 (9 mL) were added to the mixture which stirred for 18 h at 23° C. The mixture was acidified with 1N aqueous HCl. The aqueous layer was washed with CH2Cl2 (3×). The organic layers were dried with MgSO4 and concentrated to give crude ethyl N-benzyl-N-(3-chloro-4-fluorophenyl)valinate (8-2) as a brown oil. MS 364.4 found, 364.1 (M+H+) required.

Provenance & Evidence