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

HRID 54206Notes

Reaction equation

HRID 54206 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[CH3:3].[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28]CNC[CH2:24]2)=[CH:19][CH:18]=1)[CH3:15]>C1(C)C=CC=CC=1>[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:24][CH2:1][N:2]([CH2:4][C:5]3[C:13]4[C:8](=[N:9][CH:10]=[CH:11][CH:12]=4)[NH:7][CH:6]=3)[CH2:3][CH2:28]2)=[CH:19][CH:18]=1)[CH3:15]

Participants

4

Reactant 2

HCID 2314791-(4-Ethoxyphenyl)piperazineHCID 53835493-(Dimethylaminomethyl)-7-azaindole

Product 1

HCID 199584983-(4-[4-Ethoxyphenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridineYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine [prepared by the method of M. M. Robinson and B. L. Robinson, J. Am. Chem. Soc., 1955, 77, 457] (0.40 g, 2.28 mmol) and 1-(4-ethoxyphenyl)piperazine (0.495 g, 2.40 mmol) in toluene (10 ml) was heated at reflux under nitrogen for 7 h. The mixture was allowed to cool and the crystallised product collected. Recrystallisation from methanol afforded the title compound (0.513 g, 67%), m.p. 179°-180° C.; (Found: C, 71.27; H, 7.19; N, 16.59. C20H24N4O requires C, 71.40; H, 7.19; N, 16.65%); δH (DMSO-d6) 1.27 (3H, t, J 7.0 Hz, ArOCH2CH3), 2.52 (4H, m, 2×piperazinyl CH2), 2.98 (4H, m, 2×piperazinyl CH2), 3.67 (2H, s, CH2N), 3.92 (2H, q, J 7.0 Hz, ArOCH2CH3), 6.80 (4H, m, ArH), 7.04 (1H, dd, J 7.8, 4.6 Hz, 5-H), 7.37 (1H, d, J 2.1 Hz, 2-H), 8.04 (1H, dd, J 7.8, 1.3 Hz, 4-H), 8.19 (1H, dd, J 4.6, 1.3 Hz, 6-H), and 11.46 (1H, br, s, NH); m/z (CI+, NH3) 337 (M+1)+.

Workup

  1. customprepared by the method of M
  2. temperatureat reflux under nitrogen for 7 h
  3. temperatureto cool
  4. customthe crystallised product collected
  5. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-9f9fa260f7a6488084a0b33273e61319
Source dataset
uspto-grants-1997_04
Patent number
US05622950

Reaction notes

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