1-Methylpiperazine → Piperazine, 1-(3-butynyl)-4-methyl- (9CI)

HRID 417863Notes

Reaction equation

HRID 417863 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C:14]#[CH:15])(=O)=O)=CC=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([O-])(O)=O.[Na+]>ClCCCl>[CH2:12]([N:20]1[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]1)[CH2:13][C:14]#[CH:15]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 2720203-Butynyl p-toluenesulfonateHCID 516892Sodium Bicarbonate

Product 1

HCID 11593463Piperazine, 1-(3-butynyl)-4-methyl- (9CI)

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of but-3-ynyl 4-methylbenzenesulfonate (972 mg) and N-methyl piperazine (482 μL) was heated to 80 C for 4.5 h, diluted with 1,2-dichloroethane (5 mL) and heated to 70° C. for 18 h. Saturated aq. NaHCO3 was added (10 mL) and the mixture was extracted with DCM (3×40 mL), and concentrated to afford 0.70 g of 1-(but-3-ynyl)-4-methylpiperazine as a 3:2 mixture of tosylate salt and free base.

Workup

  1. temperaturewas heated to 80 C for 4.5 h
  2. extractionthe mixture was extracted with DCM (3×40 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bc2d2ada98c544b8a001f71f94e431e4
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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