4-Piperidineethanol → 2-[1-(6-Fluoro-1-isoquinolyl)-4-piperidyl]ethanol

HRID 1663034Notes

Reaction equation

HRID 1663034 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][OH:21])[CH2:15][CH2:14]1>>[F:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][OH:21])[CH2:15][CH2:14]1)=[N:3][CH:4]=[CH:5]2

Participants

3

Reactant 2

HCID 739534-PiperidineethanolHCID 219010721-Chloro-6-fluoroisoquinoline

Product 1

HCID 210969282-[1-(6-Fluoro-1-isoquinolyl)-4-piperidyl]ethanolYield 39.1%

Procedure

The process is performed as described in Example 4 (step 4.1). Starting with 1.52 g (8.39 mmol) of 1-chloro-6-fluoroisoquinoline and 1.20 g (9.23 mmol) of 2-(4-piperidyl)ethanol, and after chromatography on silica gel, eluting with a 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.90 g of pure product is obtained in the form of a yellow paste.

Workup

  1. washafter chromatography on silica gel, eluting with a 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-081355006bc8406c90f8d1c6b766bdcb
Source dataset
uspto-grants-2011_10
Patent number
US08034818B2

Reaction notes

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