Methane → HCID 19085481, compound

HRID 962444Notes

Reaction equation

HRID 962444 reaction equation
[C:1]1([O:7][CH2:8][CH2:9]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:11].Cl.[CH2:13]([N:20]([CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[CH3:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.C>O.C(N(CC)CC)C.CN(C=O)C>[ClH:11].[ClH:11].[CH2:13]([N:20]([CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:9][CH2:8][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:26][CH2:25]1)[CH3:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 68526Benzene, (2-bromoethoxy)-HCID 19085414HCID 19085414, compound

Product 1

HCID 19085481HCID 19085481, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-Bromoethyl phenyl ether (4.94 g) was added to a mixture of 4-[2-(N-benzyl-N-methylamino)ethyl]piperidine dihydrochloride (7.5 g), DMF (50 ml) and triethylamine (13.7 ml) The mixture was heated on a steam bath for 18 hours and then poured into water (300 ml) and acidified with 2M hydrochloric acid. The mixture was washed with ether then basified with 2M sodium hydroxide solution and extracted with dichloromethane to give a gum. The gum was dissolved in petroleum ether b.p. 60°-80° C., treated with charcoal and hot filtered. The filtrate was evaporated and the residual oil was dissolved in ether, acidified with ethereal hydrogen chloride, and filtered. The solid obtained was washed with ether and recrystallised from absolute ethanol to give 4-[2-(N-benzyl-N-methylamino)ethyl]-1-(2-phenoxyethyl)piperidine dihydrochloride, m.p. 276°-278° C.

Workup

  1. temperaturewas heated on a steam bath for 18 hours
  2. washThe mixture was washed with ether
  3. extractionextracted with dichloromethane
  4. customto give a gum
  5. customThe filtrate was evaporated
  6. dissolutionthe residual oil was dissolved in ether
  7. filtrationfiltered
  8. customThe solid obtained
  9. washwas washed with ether
  10. customrecrystallised from absolute ethanol

Sources & evidence

ORD record
ord-ba1b6554b6324de8812f7ced6106352a
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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