Hydrochloric Acid → HCID 19085496, compound

HRID 962450Notes

Reaction equation

HRID 962450 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH3:17])=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:30]1([O:36][CH2:37][CH2:38]Br)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[ClH:40]>CCOCC.C(N(CC)CC)C.C1(C)C=CC=CC=1>[ClH:9].[ClH:40].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([CH2:38][CH2:37][O:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:5][CH2:4]2)[CH3:17])=[CH:12][CH:11]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 7467P-ChloroacetophenoneHCID 235274-(Aminomethyl)piperidineHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 19085496HCID 19085496, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-aminomethylpiperidine (5.0 g), 4'-chloroacetophenone (6.77 g), p-toluenesulphonic acid (catalytic amount) and toluene (50 ml) was boiled under reflux for 8 hours while removing the water formed using a Dean and Stark apparatus. The mixture was cooled to ambient temperature and 2-bromoethyl phenyl ether (8.84 g) and triethylamine (6.1 ml) were added. The mixture was boiled under reflux for 2 hours and evaporated to dryness. The residue was dissolved in ethanol (100 ml) and sodium borohydride (3.4 g) was added. The mixture was boiled under reflux for 18 hours and then evaporated to dryness. The residue was dissolved in 2M hydrochloric acid, washed with ethyl acetate, basified with 5M sodium hydroxide solution and the mixture extracted with dichloromethane to give an oil. The oil was dissolved in ether and treated with ethereal hydrogen chloride solution to give a solid which was collected by filtration and recrystallised from absolute ethanol to give 4-[1-(4-chlorophenyl)ethylaminomethyl-]-1-(2-phenoxyethyl)piperidine dihydrochloride, m.p. 220° C.

Workup

  1. temperatureunder reflux for 8 hours
  2. customwhile removing the water
  3. customformed
  4. temperatureunder reflux for 2 hours
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in ethanol (100 ml)
  7. additionsodium borohydride (3.4 g) was added
  8. temperatureunder reflux for 18 hours
  9. customevaporated to dryness
  10. dissolutionThe residue was dissolved in 2M hydrochloric acid
  11. washwashed with ethyl acetate
  12. extractionthe mixture extracted with dichloromethane
  13. customto give an oil
  14. customto give a solid which
  15. filtrationwas collected by filtration
  16. customrecrystallised from absolute ethanol

Sources & evidence

ORD record
ord-1da9a18c103b43c084170592da371cac
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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