Benzyl Chloride → 2-Phenylmethoxycyclohexan-1-amine

HRID 1753990Notes

Reaction equation

HRID 1753990 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[OH:8].[OH-].[Na+].[OH-].[K+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C(C)=CC=CC=1.O>[CH2:13]([O:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]1[NH2:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 735777(1R,2R)-2-Aminocyclohexanol

Product 1

HCID 40939022-Phenylmethoxycyclohexan-1-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7237O-XyleneSolvent

Procedure

0.2 mol of trans-2-aminocyclohexanol are dissolved in 600 ml of xylene isomer mixture and heated to reflux. 0.2 mol of a 50% sodium hydroxide or potassium hydroxide solution in water is added dropwise to this solution over 15 minutes. In the course of this, the water which has been introduced and which forms is distilled off immediately. After the addition has ended, the water present in the reaction solution is distilled off further until a transition temperature of 140-141° C. is attained. Thereafter, 0.2 mol of benzyl chloride is added dropwise over 30 minutes and the solution is stirred further under reflux for two hours. After aqueous workup, the desired 2-benzyloxycyclohexylamine is obtained in 62% (GC area%) yield in the case of sodium hydroxide, and in 69% (GC area%) yield in the case of potassium hydroxide.

Workup

  1. temperatureheated to reflux
  2. distillationwhich forms is distilled off immediately
  3. additionAfter the addition
  4. distillationthe water present in the reaction solution is distilled off further until a transition temperature of 140-141° C.
  5. temperatureunder reflux for two hours

Sources & evidence

ORD record
ord-43155496d82b4802a9a3eac3b96b33f0
Source dataset
uspto-grants-2015_10
Patent number
US09169193B2

Reaction notes

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