Piperazine → 2-[{4-(2-Pyridinyl)Benzyl}Oxy]-6-(1-Piperazinyl)Pyrazine

HRID 1296669Notes

Reaction equation

HRID 1296669 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:12][CH:11]=2)[N:3]=1.N1C=CC=CC=1C1C=CC(CO)=CC=1.[NH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1C1C=CC(C=O)=CC=1>>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[N:3]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 1515239(4-(Pyridin-2-yl)phenyl)methanolHCID 15152404-Pyridin-2-ylbenzaldehydeHCID 181869352-Chloro-6-[{4-(2-pyridinyl)benzyl}oxy]pyrazine

Product 1

HCID 181869372-[{4-(2-Pyridinyl)Benzyl}Oxy]-6-(1-Piperazinyl)Pyrazine

Procedure

The title compound was prepared according to the procedure of example 50, step 2, starting from 2-chloro-6-[{4-(2-pyridinyl)benzyl}oxy]pyrazine (2.73 g, 9.16 mmol; obtained according to the procedure of example 50, step 1, starting from 4-(2-pyridinyl)benzyl alcohol*), piperazine (2.41 g, 27.9 mmol) and K2CO3 (1.33 g, 9.62 mmol) with the exception that the final filtration through alumina was omitted. The yield of the of the title compound was 2.06 g (65%) which was obtained as a beige colored oil that solidified when refrigerated. Purity 100% (HPLC). MS m/z 347 (M)+. HRMS m/z calcd for C20H21N5O (M)+ 347.1746, found 347.1749. *Obtained by reduction (NaBH4) of 4-(2-pyridyl)benzaldehyde.

Workup

  1. customobtained
  2. filtrationfiltration through alumina
  3. customwas obtained as a beige colored oil that solidified when refrigerated

Sources & evidence

ORD record
ord-b295db703f8c42608a69355c3bbef798
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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