Hydrochloric Acid → HCID 21459871, compound

HRID 1781294Notes

Reaction equation

HRID 1781294 reaction equation
C([O-])(=[O:3])C.[NH4+].[N+]([C@@H:9]1[CH2:14][CH2:13][C:12](=[O:15])[NH:11][C@H:10]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O-])=O.C[O-].[Na+].Cl>O.CO.[Cl-].[Cl-].[Cl-].[Ti+3]>[O:15]=[C:12]1[CH2:13][CH2:14][C:9](=[O:3])[CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:11]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 1417894HCID 1417894, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 21459871HCID 21459871, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 5L flask containing ammonium acetate (450g) which had been thoroughly purged with nitrogen was added a freshly prepared solution of titanium trichloride (300 g, 1.95 mol) in deoxygenated water (2.1L) with ice-bath cooling. To the resulting green solution was added a solution of trans-3-nitro-6-oxo-2-phenylpiperidine (Example 1a, 90 g, 0.409 mol) and sodium methoxide (27 g, 0.5 mol) in methanol (750 ml). The solution was stirred for 1 hr at 0° C. and for a further 1 hr at room temperature. Concentrated hydrochloric acid (240 ml) was added dropwise, and the resulting mixture extracted with ethyl acetate (1000 ml, 3×500 ml). The combined organic extracts were washed with saturated brine (1000 ml), dried (MgSO4), and evaporated under reduced pressure. The residue was suspended in ether and filtered and the pale yellow crystalline solid was washed with ether (3×100 ml) and dried in vacuo to afford 2,5-dioxo-6-phenylpiperidine (58 g, 75%): m.p. 160°-164° C.

Workup

  1. customhad been thoroughly purged with nitrogen
  2. temperaturecooling
  3. extractionthe resulting mixture extracted with ethyl acetate (1000 ml, 3×500 ml)
  4. washThe combined organic extracts were washed with saturated brine (1000 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. filtrationfiltered
  8. washthe pale yellow crystalline solid was washed with ether (3×100 ml)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-5f52b1beaf2f4650a80696f1a265442e
Source dataset
uspto-grants-1997_05
Patent number
US05633266

Reaction notes

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