Water → HCID 131710659, compound

HRID 596755Notes

Reaction equation

HRID 596755 reaction equation
[ClH:1].[C:2]1([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[C:24](=[O:25])[CH2:23][CH2:22][CH2:21][C:20]1=[O:26].C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1>[ClH:1].[C:2]1([C:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[C:24](=[O:25])[CH2:23][CH2:22][CH2:21][C:20]3=[O:26])[CH2:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27238604-Phenyl-1,2,3,6-tetrahydropyridine hydrochlorideHCID 13320447HCID 13320447, compound

Product 1

HCID 131710659HCID 131710659, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

4-Phenyl-1,2,3,6-tetrahydropyridine, hydrochloride (10g) is converted to its free base and mixed with 11.0g of N-(4-bromobutyl)glutarimide and 18g of sodium carbonate in 200 ml of toluene. The mixture is refluxed for 5 hours, cooled to 25° C, and 50 ml of water is added. After stirring for 15 minutes, the layers are separated and the organic layer is filtered through fritted glass and extracted with 10% hydrochloric acid. The acid layer is made alkaline (pH 10) with sodium hydroxide producing an insoluble gum that crystallizes on standing. The supernatant is decanted and the residue is recrystallized by dissolving in methanol and slowly diluting with an equal volume of water. An oil is produced that crystallizes on standing.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. customthe layers are separated
  3. filtrationthe organic layer is filtered through fritted glass
  4. extractionextracted with 10% hydrochloric acid
  5. customcrystallizes
  6. customThe supernatant is decanted
  7. customthe residue is recrystallized
  8. dissolutionby dissolving in methanol
  9. additionslowly diluting with an equal volume of water
  10. customAn oil is produced
  11. customthat crystallizes on standing

Sources & evidence

ORD record
ord-da36806fa662458bac934e781921e5f4
Source dataset
uspto-grants-1977_03
Patent number
US04012374

Reaction notes

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