Hydrochloric Acid → 1-(5-Iodo-2-methoxyphenyl)methanamine

To a stirred solution of 67 (500 mg, 1.9 mmol) and ammonium acetate (1.5 g, 19.4 mmol) in dry methanol (6 mL) NaCNBH3 (170 mg, 2.66 mmol) was added in one portion. The resulting mixture was stirred at room temperature for 48 h. Concentrated HCl was added until pH<2. The methanol was evaporated and the resulting white residue was dissolved in water (10 mL) and washed with Et2O (2×10 mL). The aqueous phase was then basified with aqueous KOH (45%), saturated with NaCl and extracted with CH2Cl2 (10 mL×4). The combined organic phases were dried over Na2SO4, filtered and concentrated to give 68 as a yellow oil (200 mg, 40%). 1H NMR (CDCl3, 300 MHz) δ 7.55-7.45 (m, 2H), 6.46-6.58 (m, 1H), 3.82-3.72 (m, 5H), 1.63 (br s, 2H). MS (m/e) (positive FAB) 264.1 (M+H)+, m.p. 95-97° C.

1. customThe methanol was evaporated
2. dissolutionthe resulting white residue was dissolved in water (10 mL)
3. washwashed with Et2O (2×10 mL)
4. extractionextracted with CH2Cl2 (10 mL×4)
5. dry with materialThe combined organic phases were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-b08e539ed8fb498b840bcc7d135cf4c5

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07825126B2