4-Benzylpiperidine → HCID 13322451, compound

HRID 2308752Notes

Reaction equation

HRID 2308752 reaction equation
Br[CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)=[O:4].[CH2:13]([CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[CH2:13]([CH:20]1[CH2:25][CH2:24][N:23]([CH:2]([CH3:12])[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)=[O:4])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 317384-BenzylpiperidineHCID 4992116alpha-Bromo-3-chloropropiophenone

Product 1

HCID 13322451HCID 13322451, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 26.48 g (0.107 mol) of 2-bromo-3'-chloropropiophenone in 70 ml of acetonitrile is placed in a 500 ml three-necked round-bottomed flask equipped with a pressure equalizing funnel, a calcium chloride drying tube and a magnetic stirrer, and 37.5 g (0.214 mol) of 4-benzylpiperidine are then added at ambient temperature over a period of about 20 minutes, without stirring. The mixture warms up; it is allowed to return to ambient temperature and, after 3 hours, 4-benzylpiperidine hydrobromide is crystallised by cooling the mixture on ice and triturating it. The crystals are filtered off and washed with acetonitrile (2×10 ml) and the filtrate is diluted with 200 ml of diethyl ether. Further 4-benzylpiperidine hydrobromide precipitates and is filtered off. 100 ml of 3N hydrochloric acid are added to the filtrate and the mixture is stirred. Three phases form. The two lower phases are collected, the upper phase is taken up in a few ml of water and the aqueous phase obtained is combined with the two phases previously separated off. Precipitation occurs. The mixture is cooled on ice, stirred and filtered on a glass frit and the first crop of precipitate is dried in a vacuum oven. The filtrate deposits a second precipitate, which is shown by thin layer chromatography to be the same product as the first crop. A total of 34.06 g of crystals of the hydrochloride, melting at between 189° and 198° C., is thus recovered, which is used as such in the subsequent reduction.

Workup

  1. customequipped with a pressure
  2. custom4-benzylpiperidine hydrobromide is crystallised
  3. temperatureby cooling the mixture on ice
  4. customtriturating it
  5. filtrationThe crystals are filtered off
  6. washwashed with acetonitrile (2×10 ml)
  7. additionthe filtrate is diluted with 200 ml of diethyl ether
  8. customFurther 4-benzylpiperidine hydrobromide precipitates
  9. filtrationis filtered off
  10. addition100 ml of 3N hydrochloric acid are added to the filtrate
  11. stirringthe mixture is stirred
  12. customThe two lower phases are collected
  13. customthe aqueous phase obtained
  14. custompreviously separated off
  15. customPrecipitation
  16. temperatureThe mixture is cooled on ice
  17. stirringstirred
  18. filtrationfiltered on a glass frit
  19. customthe first crop of precipitate is dried in a vacuum oven
  20. customA total of 34.06 g of crystals of the hydrochloride, melting at between 189° and 198° C., is thus recovered

Sources & evidence

ORD record
ord-1db974f0d4f9468793dddfc57e395053
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

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