Water → HCID 131710749, compound

HRID 2398078Notes

Reaction equation

HRID 2398078 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-:28].[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][NH:19][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][C:20]([OH:26])=[O:28])[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 131710749HCID 131710749, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

4-Phenyl-1,2,3,6-tetrahydropyridine hydrochloride (10 g) is converted to its free base and combined with 11.0 g of N-(4-bromobutyl)glutarimide and 18 g 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 to remove insoluble material and then extracted with 10% hydrochloric acid. The acid solution is allowed to stand in an open beaker for 1 week during which time the product precipitates out. It is filtered off and dried at 70° C, 0.1 mm of Hg, for 12 hours to yield 6.3 g of the title compound, melting point 163°-165°C.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. customthe layers are separated
  3. filtrationthe organic layer is filtered through fritted glass
  4. customto remove insoluble material
  5. extractionextracted with 10% hydrochloric acid
  6. waitto stand in an open beaker for 1 week during which time
  7. customthe product precipitates out
  8. filtrationIt is filtered off
  9. customdried at 70° C

Sources & evidence

ORD record
ord-a81e1f609e9c4812b9d7557bac6046e7
Source dataset
uspto-grants-1977_05
Patent number
US04024151

Reaction notes

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