Triethylamine → HCID 57489618, compound

HRID 2044066Notes

Reaction equation

HRID 2044066 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(CC)CC.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C1COCC1.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 57489618HCID 57489618, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 1-(4-nitrophenyl)piperazine (5 g, 24.13 mmol) and Et3N (5.04 mL, 36.2 mmol) in THF (20 mL) was added benzyl chloroformate (3.79 mL, 26.5 mmol) portion-wise at 0° C. The reaction mixture was stirred at 0° C. for 1 h and then at rt for 2 h. The reaction mixture was diluted with CH2Cl2, washed with satd NaHCO3 and water, and concentrated to give 8.06 g of benzyl 4-(4-nitrophenyl)piperazine-1-carboxylate as yellow solid. LCMS: (M+H)+=342.15.

Workup

  1. waitat rt for 2 h
  2. washwashed with satd NaHCO3 and water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-173ea060183c454a89699c323ff42c37
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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