HCID 22768460, compound → HCID 18520122, compound

HRID 1764469Notes

Reaction equation

HRID 1764469 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:29]([Mg]Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(OCC)C>[C:23]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][C:13]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([OH:16])[CH2:12][CH2:11]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 22768460HCID 22768460, compoundHCID 178419663HCID 178419663, compound

Product 1

HCID 18520122HCID 18520122, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1 part of this ketal in 5 parts of glacial acetic acid is added 0.1 part of sulfuric acid and the mixture is heated on a steam bath for 1 hour. The reaction mixture is poured into 50 parts of cold water to provide 1-[3,3-diphenyl-3-(2-pyridyl)propyl]-4-oxopiperidine. 3 Parts of this ketone in 20 parts by volume of ethyl ether and 5 parts by volume of 3 molar solution of benzylmagnesium bromide in ethyl ether are reacted under reflux for 4 hours. The mixture is cooled, quenched with water, and the ethereal layer is dried over anhydrous sodium sulfate. Removal of the ether provides 1-[3,3-diphenyl-3-(2-pyridyl)propyl]-4-benzyl-4-hydroxypiperidine, having the following structural formula ##STR22##

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe mixture is cooled
  3. customquenched with water
  4. dry with materialthe ethereal layer is dried over anhydrous sodium sulfate
  5. customRemoval of the ether

Sources & evidence

ORD record
ord-ea109324971749d38e43ac025ed604a6
Source dataset
uspto-grants-1978_09
Patent number
US04116963

Reaction notes

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