1-(3-Chloropropyl)-pyrrolidine → 7-(3-Pyrrolidin-1-yl-propoxy)-3,4-dihydro-2H-isoquinolin-1-one

HRID 2250137Notes

Reaction equation

HRID 2250137 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.Cl[CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C=O)C>[N:17]1([CH2:16][CH2:15][CH2:14][O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][NH:8][C:9]3=[O:12])=[CH:4][CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 442032017-Hydroxy-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 596405327-(3-Pyrrolidin-1-yl-propoxy)-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(3-Pyrrolidin-1-yl-propoxy)-3,4-dihydro-2H-isoquinolin-1-one is prepared from 7-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (0.48 g, 2.94 mmol) in a manner substantially analogous to Procedure A except DMF is used in place of dioxane and 1-(3-Chloro-propyl)-pyrrolidine is used instead of N-(3-chloropropyl)piperidine. Following aqueous workup, the crude material is purified by flash chromatography (Biotage 40M SiO2, elute 90/10/1 CH2Cl2/MeOH/NH4OH) to give the title compound as an off-white solid (0.17 g, 21%). MS (ES+) 275.1

Workup

  1. customFollowing aqueous workup, the crude material is purified by flash chromatography (Biotage 40M SiO2, elute 90/10/1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-3166dd898c594256b3d4f5254941b7f6
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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