1-Methylpiperazine → HCID 18321587, compound

HRID 1699282Notes

Reaction equation

HRID 1699282 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CCN(C(C)C)C(C)C.[CH3:29][C:30]([CH3:41])([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])[CH3:31]>ClCCl>[CH3:31][C:30]([CH3:41])([O:32][C:33]([N:35]1[CH2:36][CH2:37][N:38]([C:5]([N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)=[O:11])[CH2:39][CH2:40]1)=[O:34])[CH3:29]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 18321587HCID 18321587, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1.1 g of triphosgene (3.7 mMol) in 20 ml of dichloromethane, a mixture of 1.2 g (10 mMol) of 1-methyl-piperazine, 0.38 ml (22 mMol) of DIEA and 35 ml of dichloromethane was added dropwise at room temperature within 30 minutes, and then the solution of 1.9 g (10 mMol) of 1-(1,1-dimethylethoxycarbonyl)piperazine and 0.38 ml of DIEA in 20 ml dichloromethane were added. After stirring for an hour at room temperature, insoluble matter was filtered off and the filtrate evaporated down in vacuo. After purification of the raw product on silica gel (Amicon, 35-70 μm), using dichloromethane/methanol/conc. ammonia(80/20/1 v/v/v) for elution, 700 mg (22% of theory) of colourless crystals were obtained of Mp. 130° C.

Workup

  1. additionwas added dropwise at room temperature within 30 minutes
  2. filtrationinsoluble matter was filtered off
  3. customthe filtrate evaporated down in vacuo
  4. customAfter purification of the raw product on silica gel (Amicon, 35-70 μm)
  5. washammonia(80/20/1 v/v/v) for elution, 700 mg (22% of theory) of colourless crystals
  6. customwere obtained of Mp. 130° C.

Sources & evidence

ORD record
ord-5efa6a9ff9cc4b86b3c4d2d7a474b75e
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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