Diethyl Ether → cis-2,6-Dimethyl-alpha,alpha-diphenyl-1-piperidinebutanol

HRID 437383Notes

Reaction equation

HRID 437383 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCO[CH2:11][CH3:12].[CH3:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([CH3:20])[N:15]1[CH2:21][CH2:22][CH2:23][C:24]([O:26]C)=O>O>[CH3:20][C@H:16]1[CH2:17][CH2:18][CH2:19][C@@H:14]([CH3:13])[N:15]1[CH2:21][CH2:22][CH2:23][C:24]([C:12]1[CH:11]=[CH:3][CH:2]=[CH:1][CH:6]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:26]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 14810575cis-2,6-Dimethyl-1-piperidinebutyric acid, methyl esterHCID 178506676HCID 178506676, compound

Product 1

HCID 14810507cis-2,6-Dimethyl-alpha,alpha-diphenyl-1-piperidinebutanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2M solution of phenyl lithium in benzene-ether (70 to 30), 100 ml., is added to 100 ml. of dry ether with stirring under a nitrogen atmosphere. The mixture is stirred and cooled to 0°-5° while a solution of 20 g. of cis-2,6-dimethyl-1-piperidinebutyric acid, methyl ester, in 100 ml. of dry ether is added slowly over a period of 15 minutes. After the addition is complete, the mixture is stirred an additional 2.5 hours at 0°-5°, then treated dropwise with 30 ml. of water. The organic layer is separated, washed with water and extracted with an excess of dilute acetic acid. The acid extract is washed with ether, basified with aqueous sodium hydroxide, then extracted with ether. The ether extract is washed with water, dried and evaporated to give cis-2,6-dimethyl-α,α-diphenyl-1-piperidinebutanol; m.p. 90°-91° C. after two crystallizations from petroleum ether.

Workup

  1. addition, is added to 100 ml
  2. temperaturecooled to 0°-5° while a solution of 20 g
  3. additionAfter the addition
  4. stirringthe mixture is stirred an additional 2.5 hours at 0°-5°
  5. additiontreated dropwise with 30 ml
  6. customThe organic layer is separated
  7. washwashed with water
  8. extractionextracted with an excess of dilute acetic acid
  9. extractionThe acid extract
  10. washis washed with ether
  11. extractionextracted with ether
  12. extractionThe ether extract
  13. washis washed with water
  14. customdried
  15. customevaporated

Sources & evidence

ORD record
ord-37308e8eed334ee18ce3cb2242c0916e
Source dataset
uspto-grants-1977_06
Patent number
US04031101

Reaction notes

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