1-Methylpiperazine → HCID 515596, compound

HRID 2351270Notes

Reaction equation

HRID 2351270 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([N:18]2[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]2)=[O:3])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 515596HCID 515596, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-nitrophenyl chloroformate, 5.04 g (25 mMole) in 25 ml of dry ethyl acetate was added dropwise to an ice bath cooled, stirred solution of N-methylpiperazine, 5.55 ml (50 mMole), and N,N-diisopropylethylamine, 5.23 ml (30 mMole), in 50 ml of dry ethyl acetate. The ice bath was removed and stirring was continued at 22° C. for three hours. The thick reaction mixture was diluted with ethyl acetate, extracted with aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over sodium sulfate and evaporated under reduced pressure. The solid residue was recrystallized from methylene chloride hexane furnishing 3.67 g of 1-(4-nitro-phenoxycarbonyl)-4-methylpiperazine, m.p. 134°-135° C., which was characterized by nuclear magnetic resonance, mass spectra, infrared spectra and elemental analyses.

Workup

  1. temperaturecooled
  2. customThe ice bath was removed
  3. additionThe thick reaction mixture was diluted with ethyl acetate
  4. extractionextracted with aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe solid residue was recrystallized from methylene chloride hexane furnishing 3.67 g of 1-(4-nitro-phenoxycarbonyl)-4-methylpiperazine, m.p. 134°-135° C., which

Sources & evidence

ORD record
ord-5c948929d0d24d86a9195c875f35c5bc
Source dataset
uspto-grants-1989_10
Patent number
US04873224

Reaction notes

Loading…