Phenol → 1-Benzyl-4-phenoxymethylpiperidine

HRID 1291192Notes

Reaction equation

HRID 1291192 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1(O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 736802(1-Benzylpiperidin-4-yl)methanol

Product 1

HCID 189198901-Benzyl-4-phenoxymethylpiperidineYield 41.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.3 g (0.00146 mol) 1-benzyl-4-hydroxymethyl-piperidine, 0.137 g (0.00146 mol) of phenol and 0.45 g (0.0017 mol) of triphenylphosphine were dissolved in 10 ml of toluene, cooled to 10° and treated slowly with 0.264 ml (0.0017 mol) of diethyl azodicarboxylate. The mixture was stirred at 90° for 25 hrs. The solvent was removed, the residue was taken up in ethyl acetate, washed three times with 40 ml of water each time and three times with 40 ml of 2N aqueous NaOH each time and the organic phase was dried over magnesium sulfate. The solvent was removed. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:2) as the eluent. 0.17 g (41.4%) 1-benzyl-4-phenoxymethylpiperidine was obtained as white crystals; m.p. 56°-57°.

Workup

  1. temperaturecooled to 10°
  2. customThe solvent was removed
  3. washwashed three times with 40 ml of water each time and three times with 40 ml of 2N aqueous NaOH each time
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customThe solvent was removed
  6. customThe residue was chromatographed on silica gel with ethyl acetate/hexane (1:2) as the eluent

Sources & evidence

ORD record
ord-f0aaca74ce014955adb1a536b1ec0437
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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