Trifluoroacetic acid → 1-Chloro-6-(piperidin-3-yloxy)isoquinoline

HRID 1435991Notes

Reaction equation

HRID 1435991 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([O:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[C:28]([Cl:32])=[N:27][CH:26]=[CH:25]3)[CH2:16]1)=O)(C)(C)C>ClCCl>[Cl:32][C:28]1[C:29]2[C:24](=[CH:23][C:22]([O:21][CH:17]3[CH2:18][CH2:19][CH2:20][NH:15][CH2:16]3)=[CH:31][CH:30]=2)[CH:25]=[CH:26][N:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866129773-(1-Chloroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866129781-Chloro-6-(piperidin-3-yloxy)isoquinolineYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) and dichloromethane (5 ml) were added to 3-(1-chloro-isoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester (370 mg) and the mixture stirred at ambient temperature for 48 h. The mixture was concentrated in vacuo then loaded onto a pre-acidified SCX column using methanol and eluted with 2M ammonia in methanol to afford 1-chloro-6-(piperidin-3-yloxy)isoquinoline (180 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washeluted with 2M ammonia in methanol

Sources & evidence

ORD record
ord-9f26b135421341c689025e02ac179995
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

Loading…