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, 14.1mmol) 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 (2.0ml) and 2M aqueous sodium hydroxide (2.0 ml). The precipitate formed was collected, the filtrate concentrated in vacuo and the solid residue was recrystallised 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
4. customthe solid residue was recrystallised from methanol

ORD record

ord-cc7d31505777458394d732e231fa4544

Source dataset

uspto-grants-1995_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05432177