Ammonium Chloride → 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

HRID 272807Notes

Reaction equation

HRID 272807 reaction equation
C[S-].[Na+].C[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([CH2:18][N:19]([CH3:21])[CH3:20])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[NH4+].[Cl-]>CN(C=O)C>[CH3:21][N:19]([CH2:18][C:12]1([C:9]2[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH3:20]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4378561Sodium methanethiolateHCID 68575946{[4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-yl]methyl}dimethylamine

Product 1

HCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolYield 108.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of Sodium thiomethoxide (49.2 g, 0.702 mol, 5 eq) in DMF (140 ml) was added {[4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-yl]methyl}dimethylamine (35 g, 0.140 mol) and the resulting mixture was heated to 130° C. Once complete, allowed to cool to ambient temperature and saturated aqueous NH4Cl (525 ml) was added. The resultant was extracted with EtOAc (3×500 ml), dried over MgSO4, filtered and concentrated in vacuo at 35° C. to provide 4-(4-dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (intermediate 3) as a yellow solid (35.7 g, 108%) containing residual DMF and EtOAc.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe resultant was extracted with EtOAc (3×500 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo at 35° C.

Sources & evidence

ORD record
ord-c5daea3423df43b19c609aabe13b416a
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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