Sodium Bicarbonate → (trans)-3-(3-Aminocyclohexyl)phenol

HRID 1108763Notes

Reaction equation

HRID 1108763 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH2:15])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(=O)(O)[O-].[Na+].O.N>Br>[NH2:15][C@H:11]1[CH2:12][CH2:13][CH2:14][C@H:9]([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[CH2:10]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12896473Azane;hydrateHCID 69971263(trans)-3-(3-Methoxyphenyl) cyclohexylamine

Product 1

HCID 69971957(trans)-3-(3-Aminocyclohexyl)phenolYield 65.8%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

47% Hydrobromic acid (140 ml) was gradually added to (trans)-3-(3-methoxyphenyl) cyclohexylamine (14.0 g) and the mixture was refluxed for an hour. After adjusting the reaction solution to pH7 with sodium bicarbonate (powder), it was adjusted to pH9 with concentrated ammonia water. After filtering the deposited crystals by suction and washing with water, they were dried by ventilation at 45° C. for 5 hours to give 8.58 g of (trans)-3-(3-aminocyclohexyl)phenol (65.8% yield).

Workup

  1. temperaturethe mixture was refluxed for an hour
  2. filtrationAfter filtering the deposited crystals by suction
  3. washwashing with water, they
  4. customwere dried by ventilation at 45° C. for 5 hours

Sources & evidence

ORD record
ord-aa1504c96c424624a42a1867353f3bdc
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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