Potassium Carbonate → tert-Butyl 4-(quinolin-2-yl)piperazine-1-carboxylate

HRID 1294785Notes

Reaction equation

HRID 1294785 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119282-ChloroquinolineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 16117834tert-Butyl 4-(quinolin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6.1 mmol 2-chloroquinoline, 6.7 mmol piperazine-1-carboxylic acid tert-butyl ester and 12.2 mmol potassium carbonate in 15 ml acetonitrile was refluxed overnight. The reaction mixture is concentrated, water is added and the compound extracted with ethyl acetate. Chromatography (SiO2; cyclohexane/ethyl acetate 9/1) gave the title compound as a colorless solid.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture is concentrated
  3. additionwater is added
  4. extractionthe compound extracted with ethyl acetate

Sources & evidence

ORD record
ord-973b2b62d5cc429e9973871406bf722a
Source dataset
uspto-grants-2007_07
Patent number
US07241761B2

Reaction notes

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