4-Piperidineethanol → HCID 21096914, compound

HRID 1663025Notes

Reaction equation

HRID 1663025 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-3591638cf5c643aa9ec0329a7fe969ad
Source dataset
uspto-grants-2011_10
Patent number
US08034818B2

Reaction notes

Loading…