Tetrahydrofuran → HCID 16772160, compound

A mixture of 2-acetylpyridine (250 mg, 2.06 mmol), cyclopropylamine (111 mg, 1.94 mmol), anhyd tetrahydrofuran (15 mL) and acetic acid (1.5 mL) is stirred at room temperature for 10 min. MP-cyanoborohydride (1.2 g, 2.82 mmol) is added and the mixture is stirred overnight. The reaction is filtered through a Varian mega bond elut SCX and the resin washed with methanol (20 mL). The resin is then washed with 7 N methanolic ammonia (60 mL) and the eluent is evaporated. The residue is purified by chromatography on an ISCO Redisep 10 g cartridge eluting with ethyl acetate to afford cyclopropyl(1-pyridin-2-yl)ethylamine (245 mg, 73% yield) as oil. A hydrochloride salt is prepared by dissolving the amine (50 mg, 0.308 mmol) in methanol (2 mL), adding 1 M ethereal hydrochloric acid (0.8 mL), some methanol is removed, more ether added and the hydrochloride salt is collected by filtration (50 mg, 69% yield as gray solid). RT=1.69 min; MS 163 (M+1); 1H NMR (δ, ppm): 9.5 (2H, br s), 8.69 (1H, d), 7.94 (1H, dd), 7.69 (1H, d), 7.47 (1H, m), 4.59 (1H, q), 1.58 (3H, d), 0.6-0.96 (4H, m).

1. stirringthe mixture is stirred overnight
2. filtrationThe reaction is filtered through a Varian mega bond elut SCX
3. washthe resin washed with methanol (20 mL)
4. washThe resin is then washed with 7 N methanolic ammonia (60 mL)
5. customthe eluent is evaporated
6. customThe residue is purified by chromatography on an ISCO Redisep 10 g cartridge
7. washeluting with ethyl acetate

ORD record

ord-53f1a04b907d4755b5decc53be155d0f

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173682B2