1-(2-Pyridyl)piperazine → HCID 22065963, compound

HRID 1600477Notes

Reaction equation

HRID 1600477 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].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25]CNC[CH2:21]1>C1(C)C=CC=CC=1>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:1][N:2]([CH2:4][C:5]2[C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)[CH2:3][CH2:21]1

Participants

4

Reactant 2

HCID 944591-(2-Pyridyl)piperazineHCID 53835493-(Dimethylaminomethyl)-7-azaindole

Product 1

HCID 22065963HCID 22065963, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-(N,N-dimethylaminomethyl)-1H-pyrrolo[2,3-b]pyridine (258 mg, 1.39 mmol) (prepared in Example 1(a)) in toluene (10 mL) was added 1-(pyridin-2-yl)piperazine (233 mL, 250 mg, 1.53 mmol). The mixture was heated at reflux over night. Heating was discontinued and when the reaction temperature had reached room temperature the solid was filtered off and dried in vacuo to give 3-[4-(pyridin-2-yl)-piperazin-1-yl]methyl-1H-pyrrolo[2,3-b]pyridine as a colourless solid (395 mg, 93%). δH (300 MHz, CDCl3) 2.50 (4H, m, piperazinyl), 3.46 (4H, m, piperazinyl), 3.68 (2H, s), 6.61 (1H, dd, J=5.1 and 6.9), 6.78 (1H, d, J=8.6), 7.06 (1H, dd, J=4.7 and 7.8), 7.39 (1H, s), 7.51 (1H, dd, 6.9 and 8.6), 8.10 (1H, d, J=8.1), 8.12(1H, d, J=7.8), 8.22(1H, d, J=4.6),11.49(1H, br s); ESMS 294 (MH+)

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux over night
  3. temperatureHeating
  4. customhad reached room temperature
  5. filtrationwas filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3e97126b04ab4424830813af8d3a8e2d
Source dataset
uspto-grants-1999_11
Patent number
US05976497

Reaction notes

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