Methyl 4-[(chlorocarbonyl)oxy]benzoate → HCID 69022699, compound

HRID 1831307Notes

Reaction equation

HRID 1831307 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]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=1)=[O:14]>C(Cl)Cl>[ClH:12].[CH3:25][O:24][C:22]([C:19]1[CH:20]=[CH:21][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:17][CH:18]=1)=[O:23]

Participants

4

Reactant 2

HCID 854163Methyl 4-[(chlorocarbonyl)oxy]benzoateHCID 27371161-(3-Pentyl)piperazine

Product 1

HCID 69022699HCID 69022699, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 1-(1-ethylpropyl)piperazine (350 μl, 2.0 mmol) and dry DCM (15 ml) was added 4-methoxycarbonylphenyl chloroformate (430 mg, 2.0 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 (3×25 ml) and water (2×25 ml). The organic solution was concentrated and re-evaporated twice with acetonitrile. The residue was dissolved in a 0.5 N HCl solution (15 ml) and a small portion of acetonitrile. The acidic solution was concentrated and stirred with ethyl acetate (15 ml). The solid was isolated and dried to give 670 mg (90%) of the title compound as a solid.

Workup

  1. washThe reaction mixture was washed with 1 N NaOH (3×25 ml) and water (2×25 ml)
  2. concentrationThe organic solution was concentrated
  3. customre-evaporated twice with acetonitrile
  4. dissolutionThe residue was dissolved in a 0.5 N HCl solution (15 ml)
  5. concentrationThe acidic solution was concentrated
  6. stirringstirred with ethyl acetate (15 ml)
  7. customThe solid was isolated
  8. customdried

Sources & evidence

ORD record
ord-11e3d074342646738f9eaa464bcde30d
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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