Potassium Carbonate → (S)-6-[1-(2-benzyloxyethyl)piperidin-3-yloxy]-2H-isoquinolin-1-one

HRID 1436018Notes

Reaction equation

HRID 1436018 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([O:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[C:25](=[O:29])[NH:24][CH:23]=[CH:22]3)[CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([O:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[C:25](=[O:29])[NH:24][CH:23]=[CH:22]3)[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 16124479(S)-6-(piperidin-3-yloxy)-2H-isoquinolin-1-one

Product 1

HCID 68874466(S)-6-[1-(2-benzyloxyethyl)piperidin-3-yloxy]-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Benzyloxyethyl bromide (1 mol) was added to a suspension of (S)-6-(piperidin-3-yloxy)-2H-isoquinolin-1-one (30 mg, 0.12 mmol) and potassium carbonate (70mg, 4.2 mol) in N, N-dimethylformamide (500 μl) and shaken for 17 hours. The reaction was quenched with hydrochloric acid (2M) and methanol and passed down an SCX cartridge. The products were purified by preparative HPLC under basic conditions. The clean products were isolated by evaporation under reduced pressure to afford (S)-6-[1-(2-benzyloxyethyl)piperidin-3-yloxy]-2H-isoquinolin-1-one: El-MS: m/z=379.4[M+H]+.

Workup

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

Sources & evidence

ORD record
ord-51ed400adef14acc9433f2a4f002242d
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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