Piperazine → HCID 18186836, compound

HRID 1357630Notes

Reaction equation

HRID 1357630 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][CH:13]=[C:12]([N:16]([CH3:18])[CH3:17])[CH:11]=2)[N:3]=1.CN(C)C1C=C(C=CC=1)CO.[NH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C([O-])([O-])=O.[K+].[K+]>>[CH3:17][N:16]([CH3:18])[C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:9][O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[N:3]=1

Participants

5

Reactant 4

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 90133m-(Dimethylamino)benzyl alcoholHCID 18186788HCID 18186788, compound

Product 1

HCID 18186836HCID 18186836, compound

Procedure

The title compound was prepared according to the procedure of example 50, step 2, starting from 2-chloro-6-[(3-dimethylaminobenzyl)oxy]pyrazine (3.04 g, 11.5 mmol; obtained according to the procedure of example 50, step 1, starting from 3-dimethylaminobenzyl alcohol), piperazine (3.08 g, 35.7 mmol) and K2CO3 (1.59 g, 11.5 mmol) with the exception that the final filtration through alumina was omitted. The yield of the of the title compound was 2.06 g (57%) which was obtained as a beige colored oil that solidified when refrigerated. Purity 98% (HPLC). MS m/z 313 (M)+. HRMS m/z calcd for C17H23N5O (M)+ 313.1903, found 313.1910.

Workup

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

Sources & evidence

ORD record
ord-51b47543302d4e7cbd2e86b89d5fed87
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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