Ethanol → HCID 10019050, compound

HRID 1461685Notes

Reaction equation

HRID 1461685 reaction equation
FC(F)(F)C([NH:5][C:6]12O[CH:7]1[CH:8]=[CH:9][C:10]1CC=[CH:13][CH2:14][C:15]=12)=O.[C:19]1([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:31]([OH:33])[CH3:32]>>[NH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH2:14][C@@H:13]([N:28]1[CH2:27][CH2:26][CH:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:30][CH2:29]1)[C@H:31]([OH:33])[CH2:32]2

Participants

4

Reactant 3

HCID 702EthanolHCID 698734-PhenylpiperidineHCID 86745358HCID 86745358, compound

Product 1

HCID 10019050HCID 10019050, compoundYield 33%

Conditions

Temperature
45 °C

Procedure

N-(Trifluoroacetyl)-1-amino-5,8-dihydronaphthalene oxide (1.9 g, 7.4 mmol) was dissolved in 25 ml of absolute ethanol to which was added 4-phenylpiperidine (3.0 g, 19 mmol). The solution was maintained at 45° C. for 17 hours and then refluxed for 3 hours. After cooling to 23° C. for 7 hours, a crystalline solid was collected by filtration and washed with ethanol and carbon tetrachloride. A polar isomer, (±)-trans-8-amino-3-hydroxy-2-(4-phenylpiperidino)tetralin, results from deacylation during the reaction (0.78 g, 33% yield). The mother liquor was evaporated to an oil which was dissolved in carbon tetrachloride. This process was repeated in order to remove most of the ethanol. When the oil was again dissolved in carbon tetrachloride, crystallization commenced and yielded 0.7 g of 4-phenyl-piperidinium trifluoroacetate.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling to 23° C. for 7 hours
  3. filtrationa crystalline solid was collected by filtration
  4. washwashed with ethanol and carbon tetrachloride

Sources & evidence

ORD record
ord-b8e39a6abf1d419ca58666fcf22283e0
Source dataset
uspto-grants-1991_12
Patent number
US05077035

Reaction notes

Loading…