Potassium Carbonate → 4-(2-{1-[1-(4-Chloro-phenyl)-cyclobutyl]-3,4-dihydro-isoquinolin-7-yloxy}-acetyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 242052

Reaction equation

HRID 242052 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36](=[O:39])[CH2:37]Cl)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:23]([O:27][C:28]([N:30]1[CH2:31][CH2:32][N:33]([C:36](=[O:39])[CH2:37][O:22][C:19]2[CH:20]=[C:21]3[C:16]([CH2:15][CH2:14][N:13]=[C:12]3[C:8]3([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH2:11][CH2:10][CH2:9]3)=[CH:17][CH:18]=2)[CH2:34][CH2:35]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15829156tert-Butyl 4-(chloroacetyl)piperazine-1-carboxylateHCID 582462431-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol

Product 1

HCID 582463044-(2-{1-[1-(4-Chloro-phenyl)-cyclobutyl]-3,4-dihydro-isoquinolin-7-yloxy}-acetyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[1-(4-chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol (example 82) (400 mg, 1.18 mmol) and 4-(2-chloro-acetyl)-piperazine-1-carboxylic acid tert-butyl ester (404 mg, 1.54 mmol) were dissolved in N,N-dimethyl-formamide (10 ml). After addition of potassium carbonate (355 mg, 2.57 mmol) the mixture was stirred for 2 h under reflux. The solvent was removed and the residue (690 mg) was used in the next step without further purification.

Workup

  1. temperatureunder reflux
  2. customThe solvent was removed
  3. customthe residue (690 mg) was used in the next step without further purification

Sources & evidence

ORD record
ord-593aec18e6744c4bbc03311d83fcc721
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Linked notes

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