Sodium Hydroxide → HCID 12542619, compound

HRID 1648914Notes

Reaction equation

HRID 1648914 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(O)[CH2:4][CH2:3]1.[OH-].[Na+]>C(O)=O.CS(C)=O.O>[CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 12542600HCID 12542600, compound

Product 1

HCID 12542619HCID 12542619, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

A solution of 8.0 g of 1-methyl-4-(α-phenyl-2-tolyl)-4-piperidinol, Example 1, in 100 ml of 97% formic acid is refluxed with stirring for 16 hours. The solution is poured into 300 ml of water, made strongly basic with a 50% sodium hydroxide solution and the basic mixture extracted thrice with 100 ml of portions of chloroform. The combined chloroform extracts are dried and the chloroform removed leaving an oil. The oil is dissolved in 20 ml of dimethylsulfoxide. The solution is diluted with 250 ml of water leaving a cream colored solid which is recrystallized from dimethylsulfoxide to give colorless crystals, mp 55°-57.5° C. of 1-methyl-4-(α-phenyl-2-tolyl)-1,2,3,6-tetrahydropyridine.

Workup

  1. extractionthe basic mixture extracted thrice with 100 ml of portions of chloroform
  2. dry with materialThe combined chloroform extracts are dried
  3. customthe chloroform removed
  4. customleaving an oil
  5. customis recrystallized from dimethylsulfoxide

Sources & evidence

ORD record
ord-080726c9dfd340498e4e16ef0589f803
Source dataset
uspto-grants-1983_11
Patent number
US04414219

Reaction notes

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