Benzhydrol → 4-Benzhydryloxypiperidine

HRID 443797Notes

Reaction equation

HRID 443797 reaction equation
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:9]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7037BenzhydrolHCID 79341Piperidin-4-olHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 30175844-Benzhydryloxypiperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 42.0 g of diphenylmethanol, 25.25 g of 4-hydroxypiperidine and 49.4 g of p-toluenesulfonic acid monohydrate is placed in a flask fitted with a thermometer and an air condensor. The reaction vessel is connected to a vacuum pump and heated to 155°-160° until the evolution of water ceases. Upon cooling, the glassy residue is partitioned between 500 ml of diethyl ether and 200 ml of 2 N aqueous sodium hydroxide, the ethereal solution is separated and washed with water and saturated aqueous sodium chloride, dried and evaporated, to yield the 4-diphenylmethoxy-piperidine melting at 56°; (its hydrochloride, prepared in isopropanol-diethyl ether, melts at 175°-177°).

Workup

  1. customis placed in a flask
  2. customfitted with a thermometer
  3. temperatureUpon cooling
  4. customthe glassy residue is partitioned between 500 ml of diethyl ether and 200 ml of 2 N aqueous sodium hydroxide
  5. customthe ethereal solution is separated
  6. washwashed with water and saturated aqueous sodium chloride
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-0e543344b79144a4b39678db54a5a3e3
Source dataset
uspto-grants-1981_04
Patent number
US04261990

Reaction notes

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