Benzhydrol → 3-(Diphenylmethoxy)piperidine

HRID 443801Notes

Reaction equation

HRID 443801 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][CH2:19][NH:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[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][CH2:19][NH:18][CH2:17]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 7037BenzhydrolHCID 232933-HydroxypiperidineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 27624173-(Diphenylmethoxy)piperidine

Procedure

The starting material is prepared as follows. The mixture of 8.28 g of diphenylmethanol, 5.05 g of 3-hydroxypiperidine and 9.5 g of p-toluene sulfonic acid monohydrate is heated to 160°-165° while evacuating the evolving water rapidly. After the water emission ceases, the mixture is heated to said temperature for 3 hours. It is allowed to cool to room temperature and is partitioned between 2 N aqueous sodium hydroxide and diethyl ether. The organic solution is separated, washed with water and saturated aqueous sodium chloride, dried and evaporated. The residue is taken up in diethyl ether, the solution extracted with 0.1 N hydrochloric acid, the extract washed with diethyl ether and made basic with saturated aqueous ammonia. It is re-extracted with diethyl ether, the extract dried and evaporated, to yield the 3-diphenylmethoxypiperidine as an oil.

Workup

  1. customThe starting material is prepared
  2. temperatureis heated to 160°-165°
  3. customwhile evacuating the evolving water rapidly
  4. temperatureAfter the water emission ceases, the mixture is heated
  5. customfor 3 hours
  6. customis partitioned between 2 N aqueous sodium hydroxide and diethyl ether
  7. customThe organic solution is separated
  8. washwashed with water and saturated aqueous sodium chloride
  9. customdried
  10. customevaporated
  11. extractionthe solution extracted with 0.1 N hydrochloric acid
  12. washthe extract washed with diethyl ether
  13. extractionIt is re-extracted with diethyl ether
  14. customthe extract dried
  15. customevaporated

Sources & evidence

ORD record
ord-ea554102fce5434bb14c8c0a03984330
Source dataset
uspto-grants-1981_04
Patent number
US04261990

Reaction notes

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