Water → HCID 178521611, compound

HRID 725836Notes

Reaction equation

HRID 725836 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]1.O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:1]([N:9]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:10]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178511715HCID 178511715, compound

Product 1

HCID 178521611HCID 178521611, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

140 ml of benzylbromide are added dropwise to a mixture of 61 g of trans-4-amino-cyclohexanol, 350 ml of water, 350 ml of ethanol and 110 g of potassium carbonate. The mixture is then heated to boiling for 1 hour, cooled and the crystalline residue is suction filtered. The residue is taken up in 1.51 of cyclohexane, the mixture is boiled, cooled and suction filtered. Washing with cyclohexane and drying in vacuo yields 108 g (92% of theory) of trans-4-dibenzylamino-cyclohexanol.

Workup

  1. temperatureThe mixture is then heated
  2. temperaturecooled
  3. filtrationfiltered
  4. temperaturecooled
  5. filtrationsuction filtered
  6. washWashing with cyclohexane
  7. customdrying in vacuo

Sources & evidence

ORD record
ord-f6d46ffa38554db192a6f364f7d4308f
Source dataset
uspto-grants-1998_01
Patent number
US05707989

Reaction notes

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