4-Bromoisoquinoline → 2-[1-(4-Isoquinolyl)-4-piperidyl]ethanol

HRID 1663036Notes

Reaction equation

HRID 1663036 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]2)=[CH:3][N:4]=1

Participants

6

Reactant 3

HCID 737434-BromoisoquinolineHCID 739534-PiperidineethanolHCID 23676156Sodium t-butoxide

Product 1

HCID 210969212-[1-(4-Isoquinolyl)-4-piperidyl]ethanolYield 65.7%

Reagents, catalysts & solvents 2

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The process is performed according to the protocol described in Example 2 (step 2.1). Starting with 1 g (4.81 mmol) of 4-bromoisoquinoline, 0.683 g (5.29 mmol) of 2-(4-piperidyl)ethanol, 1.11 g (11.50 mmol) of sodium tert-butoxide, 0.090 g (0.144 mmol) of BINAP and 0.044 g (0.048 mmol) of tris(dibenzylideneacetone)dipalladium, and after chromatography on silica gel, eluting with a 97/3 and then 95/5 mixture of dichloromethane and methanol, 0.810 g of product is obtained in the form of a viscous green liquid.

Workup

  1. washafter chromatography on silica gel, eluting with a 97/3
  2. addition95/5 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-dc92a732f65644b3bf97d6e9e3d78db0
Source dataset
uspto-grants-2011_10
Patent number
US08034818B2

Reaction notes

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