Dimethyl-(4-piperazin-1-YL-phenyl)-amine → 3-(4-[4-Dimethylaminophenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine

HRID 54208Notes

Reaction equation

HRID 54208 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].[CH3:14][N:15]([CH3:28])[C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27]CNC[CH2:23]2)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH3:23][N:22]([CH3:27])[C:19]1[CH:20]=[CH:21][C:16]([N:15]2[CH2:28][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][CH2:14]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 4738754Dimethyl-(4-piperazin-1-YL-phenyl)-amineHCID 53835493-(Dimethylaminomethyl)-7-azaindole

Product 1

HCID 199585163-(4-[4-Dimethylaminophenyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridineYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (0.4450 g, 2.54 mmol) and 1-(4-dimethylaminophenyl)piperazine (0.55 g, 2.68 mmol) in toluene (20 ml) was heated at reflux under nitrogen for 7 h. The mixture was allowed to cool and the solid formed was collected. Recrystallisation from methanol gave the title compound (0.382 g, 45%) as colourless neddles, m.p. 199°-201° C.; (Found C, 71.32; H, 7.37; N, 20.71. C20H25N5 requires C, 71.61; H, 7.51; N, 20.88%); δH (DMSO-d6) 2.52 (4H, m, 2×piperazinyl CH2), 2.76 (6H, s, N(CH3)2), 2.95 (4H, m, 2×piperazinyl CH2), 3.67 (2H, s, CH2N), 6.66 (2H, m, ArH), 6.80 (2H, m, ArH), 7.03 (1H, dd, J 7.8, 4.7 Hz), 7.35 (1H, d, J 2.0 Hz, 2-H), 8.04 (1H, dd, J 7.8, 1.5 Hz, 4-H), 8.19 (1H, dd, J 4.7, 1.5 Hz, 6-H), and 11.41 (1H, br s, NH); m/z (CI+, NH3) 336 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 7 h
  3. temperatureto cool
  4. customthe solid formed
  5. customwas collected
  6. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-c3f912e6bb8a410f9aa872115062886d
Source dataset
uspto-grants-1997_04
Patent number
US05622950

Reaction notes

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