Dimethylformamide → 5-Bromomethyl-2chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

To a stirred solution of 5-bromomethyl-2-chloro-benzoic acid (Example 71a, 12.4 g) in dichloromethane (250 ml) and dimethylformamide (0.12 ml) at 0° C. was added oxalyl chloride (8.7 ml). The cooling bath was removed and the solution allowed to warm to room temperature. Once gas evolution had ceased the solution was concentrated in vacuo. The residue was redissolved in dichloromethane (300 ml), cooled to 0° C. and treated with diisopropylethylamine (12.4 ml) and adamantylmethylamine (7.54 ml). After 15 min. at 0° C. the solution was poured into diethyl ether (1L) and washed with 1N aqueous hydrochloric acid followed by brine. The organics were dried over magnesium sulphate and concentrated in vacuo to give the title compound as a white powder (19 g)

1. customThe cooling bath was removed
2. concentrationwas concentrated in vacuo
3. dissolutionThe residue was redissolved in dichloromethane (300 ml)
4. temperaturecooled to 0° C.
5. additiontreated with diisopropylethylamine (12.4 ml) and adamantylmethylamine (7.54 ml)
6. additionAfter 15 min. at 0° C. the solution was poured into diethyl ether (1L)
7. washwashed with 1N aqueous hydrochloric acid
8. dry with materialThe organics were dried over magnesium sulphate
9. concentrationconcentrated in vacuo

ORD record

ord-e7e2cab81d674612bc77a2bb88592a35

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06881754B2