Sodium Acetate → 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-one

HRID 840621Notes

Reaction equation

HRID 840621 reaction equation
C(O[C:4](=[O:21])[CH2:5][CH2:6][CH:7]1[CH2:12][CH:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][C:8]1=O)C.Cl.Cl.[NH2:24][CH2:25][C:26]1[NH:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].ClCCCl>[NH:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[CH2:25][N:24]1[CH:8]2[CH:7]([CH2:12][CH:11]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]2)[CH2:6][CH2:5][C:4]1=[O:21]

Participants

8

Reactant 4

HCID 517045Sodium AcetateHCID 2723957(1H-benzo[d]imidazol-2-yl)methanamine dihydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 699404643-(5-Benzyl-2-oxo-cyclohexyl)-propionic acid ethyl ester

Product 1

HCID 99075681-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-oneYield 15.7%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 0.74 g of 3-(5-benzyl-2-oxo-cyclohexyl)-propionic acid ethyl ester, 0.572 g of 2-aminomethylbenzimidazole dihydrochloride, 10 mL of 1,2-dichloroethane, 0.40 g of sodium acetate and 0.74 g of sodium triacetoxyborohydride was stirred at room temperature for 48 h. The reaction mixture was diluted with 100 mL chloroform and 40 mL saturated aqueous Na2CO3 and the layers separated. The aqueous layer was extracted with 2×25 mL of chloroform and the combined organic layers dried over magnesium sulfate and concentrated under reduced pressure. Purification by chromatography eluting with a gradient of ethyl acetate to 10% methanol in ethyl acetate gave 0.15 g of 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-one.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×25 mL of chloroform
  3. dry with materialthe combined organic layers dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography
  6. washeluting with a gradient of ethyl acetate to 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-1722bd91d3bb4acbb573d8ca93e476b8
Source dataset
uspto-grants-2002_04
Patent number
US06369076B1

Reaction notes

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