Triethylamine → benzyl N-(2-bromoethyl)carbamate

Benzyl chloroformate (26 mL, 0.176 mole) was added in one portion to a stirring mixture of bromoethylamine hydrobromide (44 g, 0.21 mole), triethylamine (64 mL, 0.46 mole), and methylene chloride (1 L) at below −40° C. After the addition, the cooling bath was removed, and the reaction was allowed to stir for 3 h. The mixture was transferred to a 2 L separatory funnel, and sequentially washed with water (2×500 mL), 2N HCl (250 mL), and water (500 mL). The resulting solution was suction filtered through a 100 g pad of silica gel and washed with methylene chloride. Evaporation of the solvents afforded the product 14 (40 g, 89%) as an oil. 1H NMR (300 MHz, CDCl3) δ 3.46 (t, 2H), 3.60 (q, 2H), 5.11 (s, 2H), 5.20 (br s, 1H), 7.35 (m, 5H).

1. additionAfter the addition
2. customthe cooling bath was removed
3. customThe mixture was transferred to a 2 L separatory funnel
4. washsequentially washed with water (2×500 mL), 2N HCl (250 mL), and water (500 mL)
5. filtrationfiltered through a 100 g pad of silica gel
6. washwashed with methylene chloride
7. customEvaporation of the solvents

ORD record

ord-8fb9fd0b092f42f2ac20575a7a4e25cd

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846688B2