Trifluoroacetic acid → (4-nitrophenyl)methyl N-(piperazine-1-carboximidoyl)carbamate;bis(2,2,2-trifluoroacetic acid)

HRID 727721Notes

Reaction equation

HRID 727721 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[NH:29])[NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>>[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[N+:26]([C:23]1[CH:22]=[CH:21][C:20]([CH2:19][O:18][C:16]([NH:15][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[NH:29])=[O:17])=[CH:25][CH:24]=1)([O-:28])=[O:27]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 140386408HCID 140386408, compound

Product 1

HCID 140386409(4-nitrophenyl)methyl N-(piperazine-1-carboximidoyl)carbamate;bis(2,2,2-trifluoroacetic acid)

Procedure

750 mg of 4-t-butoxycarbonyl-1-(4-nitrobenzyloxycarbonylamidino)piperazine [prepared as described in Preparation 92(b)] were dissolved in 12 ml of trifluoroacetic acid, and the resulting solution was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and diethyl ether was added to the residue. The powder thus formed was washed three times with diethyl ether and then dried to obtain 1010 mg of the title compound, as a colorless powder.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and diethyl ether
  2. additionwas added to the residue
  3. customThe powder thus formed
  4. washwas washed three times with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-b6befc42fd35487faf0ecd7c67fb6f92
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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