Sodium Hydroxide → 3-(4-[4-Carboxyphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine

HRID 54214Notes

Reaction equation

HRID 54214 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 199585013-(4-[4-ethoxycarbonylphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 199584903-(4-[4-Carboxyphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridineYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3-(4-[4-ethoxycarbonylphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine (0.6594 g, 1.81 mmol) in ethanol (50 ml) containing 1M aqueous sodium hydroxide (10.5 ml, 10.8 mmol) was stirred at room temperature for eight days, during which time the solid slowly dissolved. The reaction mixture was concentrated to a small volume, diluted with water and neutralised (pH 6-7) with acetic acid to give a gum which solidified on standing. The solid was collected, washed with water and dried in vacuo. Recrystallisation from dimethylformamide/water gave the title compound (0.4069 g, 67%) as a white solid, m.p. >250° C. (dec.); (Found: C, 66.96; H, 5.88; N, 16.30. C19H20N4O2.0.25H2O requires C, 66.94; H, 6.06; N, 16.44); δH (DMSO-d6) 2.51 (4H, m, 2×piperazinyl CH2), 3.27 (4H, m, 2×piperazinyl CH2), 3.68 (2H, s, CH2N), 6.93 (2H, d, J 9.0 Hz, ArH), 7.04 (1H, dd, J 7.8, 4.7 Hz, 5-H), 7.38 (1H, d, J 2.2 Hz, 2-H), 7.57 (2H, d, J 9.0 Hz, ArH), 8.06 (1H, dd, J 7.8, 1.4 Hz, 4-H), 8.20 (1H, dd, J 4.7, 1.4 Hz, 6-H), and 11.48 (1H, br s, NH); m/z (CI+, NH3) 337 (M+1)+.

Workup

  1. dissolutionslowly dissolved
  2. concentrationThe reaction mixture was concentrated to a small volume
  3. additiondiluted with water and neutralised (pH 6-7) with acetic acid
  4. customto give a gum which
  5. customThe solid was collected
  6. washwashed with water
  7. customdried in vacuo
  8. customRecrystallisation from dimethylformamide/water

Sources & evidence

ORD record
ord-4965a3445d75439e97869315a2417ad1
Source dataset
uspto-grants-1997_04
Patent number
US05622950

Reaction notes

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