Diethylene Glycol → HCID 20394496, compound

HRID 261614Notes

Reaction equation

HRID 261614 reaction equation
C(OC([N:6]1[CH2:11][CH:10]=[C:9]([CH3:12])[CH2:8][CH:7]1[C:13]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)([CH3:15])[CH3:14])=O)C.[OH-].[Na+].C(O)COCCO>O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]([CH:7]2[CH2:8][C:9]([CH3:12])=[CH:10][CH2:11][NH:6]2)([CH3:15])[CH3:14])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 20394512HCID 20394512, compound

Product 1

HCID 20394496HCID 20394496, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-ethoxycarbonyl-1,2,3,6-tetrahydro-2-[1-(4-chlorophenyl)-1-methylethyl]-4-methylpyridine (14.5 g), sodium hydroxide (15 g) and diethylene glycol (150 ml) was refluxed for 5 hours. After cooling, water was added to the reaction mixture and the resulting mixture was extracted with benzene. The extract was washed with water and dried over potassium carbonate. After removal of benzene, the residue was distilled under reduced pressure to obtain 10.7 g of a colorless viscous mass of 2-[1-(4-chlorophenyl)-1-methylethyl]-1,2,3,6-tetrahydro-4-methylpyridine.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionthe resulting mixture was extracted with benzene
  4. washThe extract was washed with water
  5. dry with materialdried over potassium carbonate
  6. customAfter removal of benzene
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-aaac6e2a0d66404391d5465b797dc2e2
Source dataset
uspto-grants-1979_08
Patent number
US04166174

Reaction notes

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