Water → 4-(Diphenylmethoxy)-1-piperidineethanol

HRID 443799Notes

Reaction equation

HRID 443799 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]1[O:23][CH2:22]1.O>CO>[OH:23][CH2:22][CH2:21][N:12]1[CH2:13][CH2:14][CH:9]([O:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 6354Ethylene OxideHCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 229894124-(Diphenylmethoxy)-1-piperidineethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The starting material is obtained as follows. The solution of 13.35 g of 4-diphenylmethoxypiperidine in 40 ml of methanol, containing 3.52 g of ethylene oxide and 0.9 ml of water, is stirred and heated in an oil bath at 42°-44° for 4 hours. The bath temperature is raised to 50° and heating and stirring are continued for an additional 3 hours. The solution is then evaporated and the residue taken up in 1 N hydrochloric acid and washed with diethyl ether. The aqueous solution is made basic with 50% aqueous sodium hydroxide and repeatedly extracted with diethyl ether. The extract is washed with brine, dried and evaporated to give the 1-(2-hydroxyethyl)-4-diphenylmethoxypiperidine, melting at 83°-85° after recrystallization from cyclohexane.

Workup

  1. customThe starting material is obtained
  2. temperatureheated in an oil bath at 42°-44° for 4 hours
  3. temperatureThe bath temperature is raised to 50°
  4. temperatureheating
  5. stirringstirring
  6. customThe solution is then evaporated
  7. washwashed with diethyl ether
  8. extractionrepeatedly extracted with diethyl ether
  9. washThe extract is washed with brine
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-5f3588da20924c4e8d4ec09107d900ff
Source dataset
uspto-grants-1981_04
Patent number
US04261990

Reaction notes

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