1-Methylpiperazine → HCID 16059508, compound

HRID 1710640Notes

Reaction equation

HRID 1710640 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][CH3:19])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][N:24]3[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]3)[CH2:6][CH2:7]2)=[CH:12][C:13]=1[O:18][CH3:19]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 210711262-Chloro-1-(4-(4-chloro-3-methoxyphenyl)piperazin-1-yl)ethanone

Product 1

HCID 16059508HCID 16059508, compound

Procedure

In a 4 mL vial was added 2-chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (1) (200 mg, 0.66 mmol, 1.0 equiv) and 1-methylpiperazine (725 μL, 6.60 mmol, 10.00 equiv). A stir bar was placed in the vial and the vial was then capped. The resultant mixture stirred at 60° C. overnight. The crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent) to yield 1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-(4-methyl-piperazin-1-yl)-ethanone (25): HPLC retention time, 0.32 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expected, 367.5, found, 367.9.

Workup

  1. customA stir bar was placed
  2. customin the vial and the vial was then capped
  3. customThe crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record
ord-0b63693623c94efcbea5658595ba5263
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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