1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-one → 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-decahydro-quinoline

HRID 840622Notes

Reaction equation

HRID 840622 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[CH:20]2[CH:15]([CH2:16][CH:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:19]2)[CH2:14][CH2:13][C:12]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[CH:20]2[CH:15]([CH2:16][CH:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:19]2)[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 99075681-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 99507351-(1H-benzimidazol-2-ylmethyl)-6-benzyl-decahydro-quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 0.15 g of 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-one in 20 mL of dry THF containing 0.1 g of lithium aluminum hydride was heated to reflux overnight, cooled in an ice bath, and quenched with 0.1 mL of 5N NaOH, then 1 mL of water. After stirring and warming to room temperature for 2 h, the mixture was filtered through a glass frit and the filtrate concentrated to dryness under reduced pressure. Chromatography using 10% methanol in chloroform gave 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-decahydro-quinoline in four bands.

Workup

  1. temperatureto reflux overnight
  2. temperaturecooled in an ice bath
  3. customquenched with 0.1 mL of 5N NaOH
  4. filtrationthe mixture was filtered through a glass frit
  5. concentrationthe filtrate concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-23d15bd442a749599ed1fc025b2ede97
Source dataset
uspto-grants-2002_04
Patent number
US06369076B1

Reaction notes

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