Potassium Carbonate → HCID 68875659, compound

HRID 1436017Notes

Reaction equation

HRID 1436017 reaction equation
[O:1]([CH2:8][CH2:9]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[C:24](=[O:28])[NH:23][CH:22]=[CH:21]3)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:1]([CH2:8][CH2:9][N:11]1[CH2:12][CH2:13][CH:14]([O:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[C:24](=[O:28])[NH:23][CH:22]=[CH:21]3)[CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 15604510SAR407899

Product 1

HCID 68875659HCID 68875659, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Phenoxyethyl bromide (1 mol eq) was added to a suspension of 6-(piperidin-4-yloxy)-2H-isoquinolin-1-one (30 mg, 0.12 mmol) and potassium carbonate (50 mgs, 3 mol) in N, N-dimethylformamide (1 ml) and shaken for 17 hours. The reactions was quenched with hydrochloric acid (2M) and methanol and passed down an SCX cartridge. The product was purified by preparative HPLC under basic conditions. The clean product was isolated by evaporation under reduced pressure to afford 6-[1-(2-phenoxyethyl)piperidin-4-yloxy]-2H-isoquinolin-1-one: El-MS: m/z=365.1 [M+H]+.

Workup

  1. customThe reactions was quenched with hydrochloric acid (2M) and methanol
  2. customThe product was purified by preparative HPLC under basic conditions
  3. customThe clean product was isolated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-bfae25d10f7c409a979391583fe4608c
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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