Aniline → Benzenamine, N-(2-methylcyclohexyl)-

HRID 612317Notes

Reaction equation

HRID 612317 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O.N1C2C=CC=CC=2N=N1.[BH4-].[Na+]>O.CO>[CH3:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 114192-MethylcyclohexanoneHCID 4311764Sodium borohydrideHCID 178418385HCID 178418385, compound

Product 1

HCID 4712370Benzenamine, N-(2-methylcyclohexyl)-Yield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a 100-mL flask, the following mixture is heated at reflux for 30 h: 9.3 g aniline, 11.2 g 2-methylcyclohexanone and 12 g benzotriazole. Then, 200 mL of methanol and 5 g of NaBH4 in portions are added to the mixture, which is then heated at reflux for 30 min. The solution is allowed to cool, and 100 mL of water are added to the mixture, which is extracted with 2×100 mL diisopropyl ether. The organic phase is recovered, dried over magnesium sulfate and reduced to dryness. In this manner, 7 g of the desired amine are produced.

Workup

  1. temperatureIn a 100-mL flask, the following mixture is heated
  2. temperatureat reflux for 30 h
  3. temperatureis then heated
  4. temperatureat reflux for 30 min
  5. temperatureto cool
  6. extractionis extracted with 2×100 mL diisopropyl ether
  7. customThe organic phase is recovered
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-61e704a2dd6541a4a35c55c83857e054
Source dataset
uspto-grants-1999_12
Patent number
US06004486

Reaction notes

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