Benzyl Bromide → trans-4-(Dibenzylamino)cyclohexanol

HRID 1963902Notes

Reaction equation

HRID 1963902 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH2:15]([N:1]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 812934-Aminocyclohexanol

Product 1

HCID 22484911trans-4-(Dibenzylamino)cyclohexanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-aminocyclohexanol (3.51 g, 23.15 mmol) and K2CO3 (12.80 g, 93 mmol) in acetonitrile (100 mL) was added benzylbromide (5.64 mL, 47.5 mmol) and the mixture was stirred at reflux for 17 hr. The crude mixture was concentrated in vacuo and the resulting residue was dissolved in water and EtOAc. The separated aqueous layer was extracted with EtOAc (2ט100 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered off and concentrated in vacuo providing crude 4-(dibenzylamino)cyclohexanol as a viscous oil, which was directly used in the next step without further purification. Yield: 6.12 g. LCMS (m/z): 296.1 [M+H]+; Retention time=0.59 min.

Workup

  1. temperatureat reflux for 17 hr
  2. concentrationThe crude mixture was concentrated in vacuo
  3. dissolutionthe resulting residue was dissolved in water
  4. extractionThe separated aqueous layer was extracted with EtOAc (2ט100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered off
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f33184635a94a4a854d2a8375450a18
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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