Trifluoroacetic acid → 1-Phenyl-3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indole

HRID 565679

Reaction equation

HRID 565679 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.FC(F)(F)C(O)=O.[C:17]1([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.N>C(O)(=O)C>[C:17]1([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([C:6]3[CH2:5][CH2:4][NH:3][CH2:8][CH:7]=3)=[CH:24]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 1820291-Phenyl-1H-indoleHCID 2723901PiperonylamineHCID 12896473Azane;hydrate

Product 1

HCID 221111271-Phenyl-3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indoleYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a heated (110° C.) mixture of 4-piperidone monohydrate hydrochloride (8.2 g), acetic acid (15 mL) and trifluoroacetic acid (30 mL) was added 1-phenyl-1H-indole (3.1 g) under nitrogen atmosphere over a period of 25 min. The mixture was stirred for 30 minutes at 120° C., then cooled and poured into ice. This was neutralized with conc. ammonia water under cooling and the product was extracted thrice with ethyl acetate. The combined extract was washed with water followed by saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was provided for the next reaction without further purification. Yield 63%. Amorphous.

Workup

  1. temperatureTo a heated
  2. temperaturecooled
  3. additionpoured into ice
  4. temperatureunder cooling
  5. extractionthe product was extracted thrice with ethyl acetate
  6. extractionThe combined extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was provided for the next reaction without further purification

Sources & evidence

ORD record
ord-962fd7bdf84944b1a7453bfae665d5d4
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Linked notes

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