Potassium Carbonate → Tert-butyl 4-(3-methoxy-4-nitrophenyl)piperazine-1-carboxylate

HRID 1503812Notes

Reaction equation

HRID 1503812 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[N:13]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:16]2[CH2:15][CH2:14][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 25918710Tert-butyl 4-(3-methoxy-4-nitrophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-fluoro-2-methoxy-1-nitrobenzene (15 g, 87 mmol), tert-butyl piperazine-1-carboxylate (19.59 g, 105.2 mmol) and potassium carbonate (24 g, 174 mmol) in N,N-dimethylformamide (150 mL) was heated at 80′C for 8 hours. After cooling to ambient temperature, the mixture was poured in water (500 mL). The precipitate was filtered and washed with ethanol to give the title compound. MS: 338 (M+H+).

Workup

  1. temperaturewas heated at 80′C for 8 hours
  2. filtrationThe precipitate was filtered
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-fd78624053b84d16a6cb9f6d22c961f2
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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