Water → HCID 69425972, compound

HRID 1352507Notes

Reaction equation

HRID 1352507 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]([CH:22]2[CH2:24][CH2:23]2)[C:19](=[O:21])[CH3:20])=[CH:10][CH:9]1[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].ClCCl.O>CO.O1CCCC1.O.O.O.O.O.O.[Ni](Cl)Cl.C1CCCCC1.C(OCC)(=O)C>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11]([N:18]([CH:22]2[CH2:24][CH2:23]2)[C:19](=[O:21])[CH3:20])[CH2:10][C@@H:9]1[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 22935748HCID 22935748, compound

Product 1

HCID 69425972HCID 69425972, compoundYield 51.7%

Reagents, catalysts & solvents 4

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 21867204Cyclohexane ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(1-benzyl-2-methyl-1,2-dihydro-quinolin-4-yl)-N-cyclopropyl-acetamide (7.5 g) in methanol (160 ml) and tetrahydrofuran (375 ml), nickel chloride hexahydrate (5.4 g) was added. After cooling at 0° C., sodium borohydride (3.41 g) was added in small portions, and then the mixture was stirred at room temperature overnight. Dichloromethane and water were added to the mixture. The organic layer was separated and the solvent was removed under reduce pressure. The crude compound was purified by flash chromatography on silicagel using cyclohexane/methanol (90/10), then (80/20), then (70/30) to give the Cis-N-(1-benzyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-cyclopropyl-acetamide (3.9 g, 51.7% yield).

Workup

  1. customThe organic layer was separated
  2. customthe solvent was removed
  3. customThe crude compound was purified by flash chromatography on silicagel

Sources & evidence

ORD record
ord-9be93b3816c54023b79cb40457382588
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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