Sodium Carbonate → HCID 11522081, compound

HRID 2358060Notes

Reaction equation

HRID 2358060 reaction equation
C[O:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]1.Cl.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH2:19]([N:16]1[CH2:17][CH2:18][CH:13]([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([C:9]([F:10])([F:11])[F:12])[C:3]=2[OH:2])[CH2:14][CH2:15]1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 57448048HCID 57448048, compound

Product 1

HCID 11522081HCID 11522081, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-[2-methoxy-3-(trifluoromethyl)phenyl]-1-propylpiperidine (0.18 g, 0.6 mmol) and pyridine hydrochloride (2 g) was heated to 190° C. and stirred for 2 h. Aqueous sodium carbonate (10%, 50 ml) and ethyl acetate (50 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phase was dried (MgSO4) and evaporated under reduced pressure to give an oil. Purification by flash column chromatography (ethyl acetate/methanol, 1:1) gave the title compound: 0.17 g (98%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 218-220° C. MS m/z (relative intensity, 70 eV) 287 (M+, 10), 259 (14), 258 (bp), 238 (15), 195 (19).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give an oil
  6. customPurification by flash column chromatography (ethyl acetate/methanol, 1:1)

Sources & evidence

ORD record
ord-062e168394f1474abf0d345a0f3dd4e6
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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