Benzyl Chloride → 2-Phenylmethoxycyclohexan-1-amine
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.C(O)CCC.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]=1Participants
Procedure
0.2 mol of trans-2-aminocyclohexanol are dissolved in 600 ml of xylene isomer mixture and 100 ml of n-butanol 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 and then the n-butanol is distilled off 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 93% (GC area%) yield in the case of sodium hydroxide, and in 92% (GC area%) yield in the case of potassium hydroxide.
Workup
- temperatureheated to reflux
- distillationwhich forms is distilled off immediately
- additionAfter the addition
- distillationthe water present in the reaction solution and then the n-butanol is distilled off until a transition temperature of 140-141° C.
- temperatureunder reflux for two hours
Sources & evidence
- ORD record
- ord-2a4283f221b44d6db17ed6c36537e7bc
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169193B2
Reaction notes
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