4-Nitrophenyl chloroformate → HCID 69022709, compound

HRID 1272037Notes

Reaction equation

HRID 1272037 reaction equation
[CH2:1]([CH:3]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[CH2:4][CH3:5])[CH3:2].[Cl:12][C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:14]>C(Cl)Cl.Cl>[ClH:12].[N+:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:13]([N:9]2[CH2:10][CH2:11][N:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH2:7][CH2:8]2)=[O:14])=[CH:21][CH:20]=1)([O-:24])=[O:23]

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 27371161-(3-Pentyl)piperazine

Product 1

HCID 69022709HCID 69022709, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 1-(1-ethylpropyl)piperazine (156 mg, 1.0 mmol) and dry DCM (10 ml) was added 4-nitrophenyl chloroformate (201 mg, 1.0 mmol). The mixture was stirred overnight at room temperature and then diluted with DCM (50 ml). The reaction mixture was washed with 1 N NaOH (3×20 ml) and water (3×20 ml) and dried (MgSO4). The organic solution was concentrated to yield an oil that was dissolved in a 0.5 N HCl solution (15 ml). The acidic solution was concentrated and re-evaporated twice with acetonitrile to give 290 mg (81%) of the title compound as a solid. M.p. 251–253° C.

Workup

  1. washThe reaction mixture was washed with 1 N NaOH (3×20 ml) and water (3×20 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationThe organic solution was concentrated
  4. customto yield an oil that
  5. concentrationThe acidic solution was concentrated
  6. customre-evaporated twice with acetonitrile

Sources & evidence

ORD record
ord-3d65a3ff9596404daf14dd79e4b0cd09
Source dataset
uspto-grants-2007_04
Patent number
US07208497B2

Reaction notes

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