Toluene → (Cyclohexyl)(1-phenylcyclobutyl)methylamine

HRID 1249177Notes

Reaction equation

HRID 1249177 reaction equation
[C:1]1([C:7]2([C:11]#[N:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]1([Mg]Br)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C1(C)C=CC=CC=1.[BH4-].[Na+]>CCOCC.C(O)C.O>[CH:13]1([NH:12][CH2:11][C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:10][CH2:9][CH2:8]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 844001-PhenylcyclobutanecarbonitrileHCID 4311764Sodium borohydrideHCID 178419651HCID 178419651, compound

Product 1

HCID 20225059(Cyclohexyl)(1-phenylcyclobutyl)methylamine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
90 °C

Procedure

A solution of 1-phenyl-1-cyclobutanecarbonitrile (30 g) in ether (100 ml) was added dropwise to a stirred solution of cyclohexylmagnesium bromide [prepared from cyclohexyl bromide (62.3 g) and magnesium (9.5 g) in ether (200 ml)]. The ether was replaced with toluene, and the mixture was stirred at 90° C. for 24 hours. Sodium borohydride (7.3 g) was added as a slurry in ethanol (200 ml) and the mixture was heated under reflux for 3 hours. The cooled mixture was acidified, basified, diluted with ether and water, and filtered (Celite). The organic layer was separated and the aqueous layer was extracted with ether. The combined extracts were washed, dried and the solvent removed by evaporation to give (cyclohexyl)(1-phenylcyclobutyl)methylamine which was isolated by conversion into a hydrochloride salt.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationfiltered (Celite)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ether
  6. washThe combined extracts were washed
  7. customdried
  8. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-851fc8f3c9d84f578e6e955e21a40dd1
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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