4-Piperidineethanol → HCID 21096914, compound

HRID 1350556Notes

Reaction equation

HRID 1350556 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N: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+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:2]1([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 739534-PiperidineethanolHCID 140539Isoquinoline, 1-chloro-HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 21096914HCID 21096914, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

4.17 g (25.50 mmol) of 1-chloroisoquinoline, 3.62 g (28 mmol) of 2-(4-piperidyl)ethanol, 5.90 g (61.20 mmol) of sodium tert-butoxide and 0.476 g (0.765 mmol) of BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) suspended in 50 ml of toluene are introduced under an inert atmosphere. 0.233 g (0.255 mmol) of tris(dibenzylideneacetone)dipalladium is then added. The reaction mixture is then refluxed for 12 hours.

Workup

  1. additionare introduced under an inert atmosphere
  2. temperatureThe reaction mixture is then refluxed for 12 hours

Sources & evidence

ORD record
ord-dc81d001e39346d6a5b0c7f12836b4ff
Source dataset
uspto-grants-2007_05
Patent number
US07214798B2

Reaction notes

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