Methanol → Methanone, [4-(phenoxymethyl)-1-piperidinyl]phenyl-

HRID 1389238Notes

Reaction equation

HRID 1389238 reaction equation
C[O-].CO.[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26]Cl)[CH2:22][CH2:21]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)C>[C:12]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][O:11][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:22][CH2:21]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 996PhenolHCID 3826051MethoxideHCID 11118098(4-(Chloromethyl)piperidin-1-yl)(phenyl)methanone

Product 1

HCID 20298875Methanone, [4-(phenoxymethyl)-1-piperidinyl]phenyl-Yield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 28 ml of 30% sdium methanolate solution and 50 ml of methanol are added 14.1 g (0.15 mole) of phenol. The reaction mixture is evaporated in a vacuum and the residue is taken up in 120 ml of N,N-dimethyl formamide, 35.5 g (0.15 mole) of N-benzoyl-4chloromethylpiperidine are added thereto and the reaction mixture is stirred for 12 hours at 60°-70° C. After cooling, the reaction mixture is mixed with diethyl ether, washed with water and dilute aqueous sodium hydroxide solution, dried over anhydrous sodium sulfate and evaporated in a vacuum. The oily residue is triturated with diethyl ether/ligroin. There are obtained 23.0 g of N-benzoyl-4-phenoxymethylpiperidine (52% of theory); m.p. 95°-96° C.

Workup

  1. customThe reaction mixture is evaporated in a vacuum
  2. temperatureAfter cooling
  3. washwashed with water and dilute aqueous sodium hydroxide solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in a vacuum
  6. customThe oily residue is triturated with diethyl ether/ligroin

Sources & evidence

ORD record
ord-b8dadb263c434b31aefac5fbbe20a885
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

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