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

HRID 1647402Notes

Reaction equation

HRID 1647402 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, 14.1mmol) 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)+.

Workup

  1. customThe precipitate formed
  2. customwas collected
  3. concentrationthe filtrate concentrated in vacuo
  4. customthe solid residue was recrystallised from methanol

Sources & evidence

ORD record
ord-cc7d31505777458394d732e231fa4544
Source dataset
uspto-grants-1995_07
Patent number
US05432177

Reaction notes

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