Cyclohexanone → cyclohexyl-(3-methoxyphenyl)-amine

HRID 2393620Notes

Reaction equation

HRID 2393620 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1.[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])O.[Na+]>ClC(Cl)C.C(O)(=O)C>[CH:12]1([NH:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH3:3])[CH:6]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 108243-MethoxyanilineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 11344754cyclohexyl-(3-methoxyphenyl)-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent2×

Procedure

Under ice cooling, 45 ml of acetic acid was added dropwise over 1 hour to 300 ml of a dichloroethane suspension of 8 g of sodium borohydride. To said mixture were added slowly a solution of 17.48 g of m-anisidine and 16 ml of cyclohexanone in 50 ml of dichloroethane, and the mixture was stirred at room temperature for 40 minutes. The reaction mixture was poured into an aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed, dried and then purified by silica gel column chromatography [ethyl acetate-hexane (1:5)] to afford 29.37 g of cyclohexyl-(3-methoxyphenyl)-amine as an oil. IR (Neat) (cm-1): 3400, 2920, 2850, 1615, 1510, 1500, 1450, MS (m/z): 205 (M+), 162.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed
  3. customdried
  4. custompurified by silica gel column chromatography [ethyl acetate-hexane (1:5)]

Sources & evidence

ORD record
ord-0c6f8c11002646c689da79ff4c9e1873
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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