Benzaldehyde → HCID 19085487, compound

HRID 962441Notes

Reaction equation

HRID 962441 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:28]1([O:34][CH2:35][CH2:36]Br)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[ClH:38]>CCOCC.C(N(CC)CC)C.O.C1(C)C=CC=CC=1>[ClH:38].[ClH:38].[CH2:9]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:36][CH2:35][O:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:5][CH2:4]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

10

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 235274-(Aminomethyl)piperidineHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 19085487HCID 19085487, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-aminomethylpiperidine (7.0 g), benzaldehyde (5.77 g), toluene (70 ml) and a catalytic amount of p-toluenesulphonic acid was boiled under reflux for 7 hours with water removal using a Dean and Stark apparatus. The mixture was cooled to ambient temperature. 2-Bromoethyl phenyl ether (12.34 g) and triethylamine (8.5 ml) were added and the mixture was boiled under reflux for 5 hours. The mixture was evaporated to dryness and the residue dissolved in absolute ethanol (100 ml). Sodium borohydride (4.6 g) was added and the mixture was boiled under reflux for 18 hours. The mixture was evaporated to dryness and the residue partitioned between 2M hydrochloric acid and ethyl acetate. The aqueous layer was separated and basified with concentrated sodium hydroxide solution. This mixture was extracted with dichloromethane to give an oil which was dissolved in ether and treated with ethereal hydrogen chloride solution. A solid was collected by filtration and recrystallised from IMS to give 4-(N-benzylaminomethyl)-1-(2-phenoxyethyl)piperidine dihydrochloride, m.p. 246°-247° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe mixture was evaporated to dryness
  3. dissolutionthe residue dissolved in absolute ethanol (100 ml)
  4. additionSodium borohydride (4.6 g) was added
  5. temperatureunder reflux for 18 hours
  6. customThe mixture was evaporated to dryness
  7. customthe residue partitioned between 2M hydrochloric acid and ethyl acetate
  8. customThe aqueous layer was separated
  9. extractionThis mixture was extracted with dichloromethane
  10. customto give an oil which
  11. filtrationA solid was collected by filtration
  12. customrecrystallised from IMS

Sources & evidence

ORD record
ord-790ae845c6d7484ab88a1b6c638b4119
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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