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

HRID 33165

Reaction equation

HRID 33165 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-a686448e25f6428e9d95799ac3023fb6
Source dataset
uspto-grants-2008_09
Patent number
US07429585B2

Linked notes

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