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

HRID 54215Notes

Reaction equation

HRID 54215 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C[O:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][N:31]([CH2:34][C:35]3[C:43]4[C:38](=[N:39][CH:40]=[CH:41][CH:42]=4)[NH:37][CH:36]=3)[CH2:30][CH2:29]2)=[CH:24][CH:23]=1)=O.[OH-].[Na+]>O1CCCC1.O.CO>[OH:19][CH2:20][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][N:31]([CH2:34][C:35]3[C:43]4[C:38](=[N:39][CH:40]=[CH:41][CH:42]=4)[NH:37][CH:36]=3)[CH2:30][CH2:29]2)=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 199585053-(4-[4-methoxycarbonylphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 199585153-(4-[4-Hydroxymethylphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridineYield 74.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-56bc443fcf574717a41692ba9287bc42
Source dataset
uspto-grants-1997_04
Patent number
US05622950

Reaction notes

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