Sodium Bicarbonate → HCID 11658423, compound

HRID 2218559Notes

Reaction equation

HRID 2218559 reaction equation
[C:1]1(C)C=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=O.[C:15]([O-])(=O)[CH3:16].[NH4+].C([BH3-])#[N:21].[Na+].C([O-])(O)=O.[Na+]>CO>[C:15]1([CH3:16])[CH:5]=[CH:4][CH:3]=[C:2]([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[NH2:21])[CH:1]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 30480412-(2-Methylphenyl)cyclohexan-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 11658423HCID 11658423, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2-o-tolyl-cyclohexanone (0.22 g) in methanol (30 ml) was added ammonium acetate (0.90 g) and the reaction was allowed to stir at room temperature for 16 hours. After such time sodiumcyanoborohydride (91 mg) was added to the reaction mixture and stirred for 10 minutes. The reaction mixture was then treated with a saturated aqueous solution of NaHCO3, and extracted with ethyl acetate (2×50 ml). The combined organic phases were dried over sodium sulfate, concentrated in vacuo and purified by column chromatography to yield (cis) 2-m-tolyl-cyclohexylamine (35 mg) MS(ISP) 190.3 (M+H)+ and (trans) 2-m-tolyl-cyclohexylamine MS(ISP) 190.3 (M+H)+.

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-e1f8ea1fadd549ee9908f0e27f01f810
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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