Potassium Carbonate → {4-[2-(Dimethylamino)-1-(1-hydroxy cyclohexyl)ethyl]phenoxy}methyl pivalate

HRID 1591800Notes

Reaction equation

HRID 1591800 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH:4]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:5]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:20]([O:26][CH2:27]Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:20]([O:26][CH2:27][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH:4]([C:5]2([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:3][N:2]([CH3:1])[CH3:19])=[CH:17][CH:16]=1)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 125017Desvenlafaxine

Product 1

HCID 9821087{4-[2-(Dimethylamino)-1-(1-hydroxy cyclohexyl)ethyl]phenoxy}methyl pivalate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol (1 g, 3.79 mmol), chloromethyl pivalate (0.75 g, 5 mmol), anhydrous K2CO3 (0.7 g, 5 mmol) and KI (75 mg, 0.5 mmol) were stirred in acetonitrile (50 mL) and refluxed overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The ethyl acetate was dried (MgSO4) and evaporated to give the title compound as a minor component.

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-1fa8cf2e261d4cc88799c5a29494219f
Source dataset
uspto-grants-2007_11
Patent number
US07291646B2

Reaction notes

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