Hydrochloric Acid → HCID 18008936, compound

Temperature

80 °C

A stirred mixture of benzyl-(4-bromo-2-nitro-phenyl)-(2-iodo-ethyl)-amine (23.55 g, Reference Example 7), tin(II) chloride dihydrate (41.48 g), hydrochloric acid 12N (21.28 ml) and distilled water (45 ml) was heated to 80° C. for 1 hour then cooled to room temperature and then treated with distilled water (200 ml). The reaction mixture was neutralized to pH 7-8 by addition of an 32% aqueous ammonia solution (50 ml) and filtered through a pad of celite. The filter pad was washed three times with dichloromethane (250 ml). The filtrate and washings were combined. The organic phase was separated, then washed four times with distilled water (200 ml), then dried over magnesium sulphate and then evaporated under reduced pressure (2.7 kPa) at 40° C. The resulting brown oil (14.47 g) was subjected to flash chromatography on silica (0,040-0,063 mm) eluting initially with a mixture of cyclohexane and ethyl acetate (9:1, v/v) and then with a mixture of cyclohexane and ethyl acetate (7:3, v/v) to give the title compound (3.28 g) as a tan solid. 1H NMR, 300 MHz, (CD3)2SO: δ3.1 (broad s, 4H); 4.2 (s, 2H); 5.6 (broad s, 1H); 6.1 (d, J=8 Hz, 1H); 6.2 (dd, J=8 Hz and J=1.5 Hz, 1H); 6.3 (d, J=1.5 Hz, 1H); 7.25 (m, 5H). MS (EI): M+ 304 and 302 (100%), 213 and 211 (100%), 132 (85%), 91 (60%).

1. distillationdistilled water (45 ml)
2. temperaturethen cooled to room temperature
3. additiontreated with distilled water (200 ml)
4. additionThe reaction mixture was neutralized to pH 7-8 by addition of an 32% aqueous ammonia solution (50 ml)
5. filtrationfiltered through a pad of celite
6. washThe filter pad was washed three times with dichloromethane (250 ml)
7. customThe organic phase was separated
8. washwashed four times with distilled water (200 ml)
9. dry with materialdried over magnesium sulphate
10. customevaporated under reduced pressure (2.7 kPa) at 40° C
11. washeluting initially with a mixture of cyclohexane and ethyl acetate (9:1
12. additionv/v) and then with a mixture of cyclohexane and ethyl acetate (7:3

ORD record

ord-1f078eb8dbdb42e38d74e3de90eb1f9c

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06632814B1