1-(3-Pentyl)piperazine → 4-(1-Ethylpropyl)piperazine-1-carboxylic Acid 2-nitrophenyl Ester Hydrochloride

HRID 1272045Notes

Reaction equation

HRID 1272045 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][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])=[O:14]>C(Cl)Cl>[ClH:12].[N+:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][C:13]([N:9]1[CH2:10][CH2:11][N:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH2:7][CH2:8]1)=[O:14])([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 27371161-(3-Pentyl)piperazineHCID 34143642-Nitrophenyl chloroformate

Product 1

HCID 690262004-(1-Ethylpropyl)piperazine-1-carboxylic Acid 2-nitrophenyl Ester HydrochlorideYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 1-(1-ethylpropyl)piperazine (175 μl, 1.0 mmol) and dry DCM (10 ml) was added 2-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 (3×25 ml) and water (2×25 ml). The organic solution was concentrated and the residue was dissolved in a 0.5 N HCl solution (15 ml). The acidic solution was concentrated and stirred with ethyl acetate (15 ml). The solid was isolated and dried to give 310 mg (86%) of the title compound as a solid. M.p. 251–253° C.

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. dissolutionthe residue was dissolved in a 0.5 N HCl solution (15 ml)
  4. concentrationThe acidic solution was concentrated
  5. stirringstirred with ethyl acetate (15 ml)
  6. customThe solid was isolated
  7. customdried

Sources & evidence

ORD record
ord-d758d26616304b4393a18bb97c5304cd
Source dataset
uspto-grants-2007_04
Patent number
US07208497B2

Reaction notes

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