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

HRID 1776015Notes

Reaction equation

HRID 1776015 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=1)[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([O:16][CH2:14][CH3:15])=[O:25])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

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-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of piperazine-1-carboxylic acid tert-butyl ester (18.6 g, 0.1 mol), 4-fluoro-benzoic acid ethyl ester (16.8 g, 1 mol) and potassium carbonate (0.15 mol) in dimethylsulfoxide (100 mL) was stirred at 120° C. for 24 h. The reaction mixture was cooled to room temperature and poured into water (1 L). The solid precipitate was filtered, washed with water, and concentrated to dryness to provide the title compound (20 g, 60% yield) as a white solid. 1H NMR (CDCl3, 400 MHz) δ (ppm) 7.91 (d, 2H), 6.83 (d, 2H), 4.30 (q, 2H), 3.55 (m, 4H), 3.26 (m, 4H), 1.46 (s, 9H), 1.32 (t, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid precipitate was filtered
  3. washwashed with water
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c8e6f44236794fd29a5e7be2655e679c
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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