Water → tert-Butyl 4-(4-(ethoxycarbonyl)phenyl)piperazine-1-carboxylate

HRID 1968598Notes

Reaction equation

HRID 1968598 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)[CH3:2].[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+].O>CS(C)=O>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([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]=1)=[O:12])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11709764tert-Butyl 4-(4-(ethoxycarbonyl)phenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of ethyl-4-fluorobenzoate (16.8 g, 0.1 mol), tert-butyl piperazine-1-carboxylate (18.6 g, 0.1 mol) and potassium carbonate (20.7 g, 0.15 mol) in dimethylsulfoxide (100 mL) was stirred under N2 at 120° C. for 10 hours. The reaction mixture was cooled to room temperature and poured into water (1 L). The solid product was filtered off, washed with water and dried in vacuum oven overnight at 40° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid product was filtered off
  3. washwashed with water
  4. customdried in vacuum oven overnight at 40° C.

Sources & evidence

ORD record
ord-72f12ca1c24449919249de9b6621eb31
Source dataset
uspto-grants-2013_04
Patent number
US08426422B2

Reaction notes

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