2-Benzylidenecyclohexanone → HCID 6443325, compound

HRID 1906430Notes

Reaction equation

HRID 1906430 reaction equation
[C:1]1([CH:7]=[C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+]>CO>[C:1]1(/[CH:7]=[C:8]2/[CH:9]([NH2:21])[CH2:10][CH2:11][CH2:12][CH2:13]/2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 989262-BenzylidenecyclohexanoneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 6443325HCID 6443325, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
10 °C

Procedure

Molecular sieve (size 3A, 2 g) was added to a solution of 2-(phenylmethylene)cyclohexanone (1.86 g, 0.01 mole) in 20 ml of methanol, followed by a solution of ammonium acetate (7.7 g, 0.1 mole) in 20 ml of methanol. The mixture was cooled to about 10° C., and a solution of sodium cyanoborohydride in 20 ml of methanol was added during five minutes. The mixture was stirred at ambient temperature for 19 hours. The mixture was filtered, and the filtrate was cooled and brought to pH 11 by the addition of 20% aqueous sodium hydroxide. The methanol was evaporated and the mixture was extracted with ether. The extract was washed with water (water layer discarded) and then with three 10 ml portions of 10% aqueous hydrochloric acid. Water was added to dissolve the resulting solid. The aqueous acidic layer was cooled, basified with sodium hydroxide and extracted with chloroform. The chloroform extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated to give 1.2 g of (±)-(E)-2-(phenylmethylene)cyclohexylamine which was identical (by tlc, UV, and nmr comparison) to the amine prepared in Part D of Example 1 above.

Workup

  1. filtrationThe mixture was filtered
  2. temperaturethe filtrate was cooled
  3. additionbrought to pH 11 by the addition of 20% aqueous sodium hydroxide
  4. customThe methanol was evaporated
  5. extractionthe mixture was extracted with ether
  6. washThe extract was washed with water (water layer discarded)
  7. additionWater was added
  8. dissolutionto dissolve the resulting solid
  9. temperatureThe aqueous acidic layer was cooled
  10. extractionextracted with chloroform
  11. extractionThe chloroform extract
  12. washwas washed with water and saturated sodium chloride solution
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customevaporated

Sources & evidence

ORD record
ord-728ccfd72d3741a3b8afd31e386d169d
Source dataset
uspto-grants-1987_03
Patent number
US04652559

Reaction notes

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