Methanol → 4-(Phenoxymethyl)piperidine

HRID 1389241Notes

Reaction equation

HRID 1389241 reaction equation
C[O-].[Na+].CO.[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.Cl[CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C(OCC)C.CN(C)C=O>[O:12]([CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 996PhenolHCID 10942334Sodium MethoxideHCID 124281464-(Chloromethyl)piperidine--hydrogen chloride (1/1)

Product 1

HCID 30174444-(Phenoxymethyl)piperidineYield 32.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 28 ml of 30% sodium methanolate solution and 50 ml methanol, there are added 14.1 g (0.15 mole) of phenol. The reaction mixture is evaporated, mixed with 50 ml of N,N-dimethyl formamide and 7.8 g (0.05 mole) of 4-chloromethylpiperidine hydrochloride and heated for 18 hours at 70°-80° 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. There are obtained 3.1 g of 4-phenoxymethylpiperidine (32% of theory); m.p. 41°-42° C.

Workup

  1. customThe reaction mixture is evaporated
  2. temperatureheated for 18 hours at 70°-80° C
  3. temperatureAfter cooling
  4. washwashed with water and dilute aqueous sodium hydroxide solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in a vacuum

Sources & evidence

ORD record
ord-6cee14ea25ac46cbbfb76d895297a9e5
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

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