Toluene → 3-(4-[4-Hydroxymethylphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine

A solution of diisobutylaluminium hydride in toluene (1.5M, 9.4 ml, 14.1 mmol) was added to a solution of 3-(4-[4-methoxycarbonylphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine (1.64 g, 4.68 mmol) in tetrahydrofuran (100 ml) and the resultant mixture stirred at room temperature for forty minutes. Methanol (3.3 ml) was added, followed by water (2.0 ml) and 2M aqueous sodium hydroxide (2.0 ml). The precipitate formed was collected, the filtrate concentrated in vacuo and the solid residue was recrystallixed from methanol to afford the title compound (1.12 g, 74%), m.p. 207°-209° C. (dec.); (Found: C, 69.48; H, 7.00; N, 16.61. C19H22N4O.0.3 MeOH requires C, 69.82; H, 7.04; N, 16.87%); δH (DMSO-d6) 2.52 (4H, m, 2×piperazinyl CH2), 3.08 (4H, m, 2×piperazinyl CH2), 3.68 (2H, CH2N), 4.36 (2H, d, J 5.6 Hz, CH2OH 4.92 (1H, t, J 5.6 Hz, CH2OH), 6.85 (2H, d J 8.7 Hz, ArH), 7.05 (1H, dd, J 7.9, 4.7 Hz, 5-H), 7.13 (2H, d, J 8.7 Hz, ArH), 7.37 (1H, d, J 2.2 Hz, 2-H), 8.05 (1H, br d, J 7.9 Hz, 4-H), 8.19 (1H, dd, J 4.7, 1.5 Hz, 6-H), and 11.47 (1H, br s, NH); m/z (CI+, NH3) 323 (M+1)+.

1. customThe precipitate formed
2. customwas collected
3. concentrationthe filtrate concentrated in vacuo

ORD record

ord-56bc443fcf574717a41692ba9287bc42

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05622950