Triethylamine → n-(4-Bromobutyl)-dihydro-2-naphtylcarboxamide

Participants

Reaction Steps

A mixture of the acid (A1) (226 mg, 1.3 mmol), oxalyl chloride (0.14 mL, 1.56 mmol) and two drops of DMF was stirred at room temperature in CH2Cl2 (20 mL) for 2 h. The solvent was evaporated and the residue was used in the next step. To a mixture of aminobutanol (0.13 mL, 1.43 mmol) and triethylamine (0.54 mL, 3.9 mmol) in CH2Cl2 (5 mL) was added a solution of the acid chloride (1.3 mmol) in CH2Cl2 (2 mL). After 12 h the solvent was evaporated and the residue taken in AcOEt (10 mL) washed with H2O, dried and concentrated. The residual solid D1 (300 mg, 90%) was used in the next step. A solution of the hydroxy adduct (300 mg, 1.22 mmol) in CH3CN (10 mL) was cooled at 0° C., and CBr4 (606 mg, 1.83 mmol) and PPh3 (480 mg, 1.83 mmol) were added. After 12 h stirring AcOEt (50 mL) was added and the organic layer was washed with NaOH (20 ml, 1 N), dried and concentrated in vacuo to give the title compound E1 as a solid (240 mg, 64%) after purification by chromatography. 1H NMR (CDCl3 200 MHz): δ 1.70-2.02 (m, 4H), 2.55-260 (m, 2H), 2.86-2.92 (m, 2H), 3.42-3.49 (m, 4H), 5.99 (s, 1H), 7.15-7.27 (m, 4H).

Provenance & Evidence