Sodium Hydroxide → HCID 178483999, compound

HRID 657619Notes

Reaction equation

HRID 657619 reaction equation
Cl.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][CH3:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].O1CCOC[CH2:20]1>C=O.[Na+].P(O)(O)[O-]>[CH3:16][N:15]([CH3:20])[C@H:12]1[CH2:13][CH2:14][C@H:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 312751,4-DioxaneHCID 178484788HCID 178484788, compound

Product 1

HCID 178483999HCID 178483999, compound

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 23701735Sodium dihydrogen phosphiteSolvent

Procedure

To a solution of trans-4-(4-hydroxyphenyl)-N-methylcyclohexanamine, hydrochloride (1.15 g) in dioxane (50 mL), aqueous formaldehyde solution (3.7 mL, 37%) and phosphorous acid monosodium salt (49 mL, 1N) is added concentrated aqueous sodium hydroxide solution until pH is neutral. The solution is stirred at a temperature close to 60° C. for 2 h, cooled to room temperature and brought to pH 7-8 by addition of concentrated aqueous sodium hydroxide solution. Evaporation of dioxane causes precipitation. The precipitate is filtrated and washed with water then diethyl ether to give 1.78 g of trans-N,N-dimethyl-4-(4-hydroxyphenyl)cyclohexanamine as a white solid.

Workup

  1. customclose to 60° C. for 2 h
  2. customEvaporation of dioxane
  3. customprecipitation
  4. filtrationThe precipitate is filtrated
  5. washwashed with water

Sources & evidence

ORD record
ord-924767e7af244352b37ea88e4b40b4ab
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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