HCID 10826203, compound → 2-Phenyl-3-(4-piperidinyl)-1H-indole

HRID 429186Notes

Reaction equation

HRID 429186 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][CH2:2]1>[Pd].CO.O>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 10826203HCID 10826203, compound

Product 1

HCID 98820672-Phenyl-3-(4-piperidinyl)-1H-indoleYield 75.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-(1,2,3,6-Tetrahydropyridin-4-yl)-2-phenyl-1H-indole (25 g, 91 mmol), palladium on carbon (10% w/w, 2.5 g) and NH4HCO2 (57 g, 0.72 mol) were refluxed in MeOH (300 ml) for 8 h. Palladium on carbon (10% w/w, 1.25 g) and NH4HCO2 (29 g, 0.36 mol) were added, and refluxing continued for 8 h. The mixture was cooled, filtered, and evaporated to give a white solid. This was suspended in H2O (1 l) and 1M NaOH (100 ml), and the mixture extracted with CH2Cl2 (5×150 ml). The combined organic layers were washed with water and brine, dried, and evaporated in vacuo to give a white solid, which was recrystallised from MeOH (300 ml) and H2O (100 ml) to give the title compound (19 g, 75%) as white crystals, mp 187-188° C. Oxalate salt, white crystals, mp 209-211° C. (from EtOH). Found C, 69.09; H, 6.65; N, 7.52. C19H20N2. C2H2O4 requires C, 68.84; H, 6.05; N, 7.65%; δH (360 MHz, d6-DMSO) 1.80 (2H, d, J 13, NCH2CHAHB), 2.30-2.50 (2H, m, NCH2CHAHB), 2.91 (2H, t, J 12, NCHAHB), 3.10-3.20 (1H, m, CH2CH), 3.32 (2H, d, J 12, NCHAHB), 6.98 (1H, t, J 7, indole-H), 7.08 (1H, t, J 7, indole-H), 7.20-7.50 (6H, m, ArH), 7.88 (1H, d, J 7, ArH), 11.3 (1H, br s, indole NH); m/z (ES+) 277 (M++H).

Workup

  1. temperaturerefluxing
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customevaporated
  5. customto give a white solid
  6. extraction1M NaOH (100 ml), and the mixture extracted with CH2Cl2 (5×150 ml)
  7. washThe combined organic layers were washed with water and brine
  8. customdried
  9. customevaporated in vacuo
  10. customto give a white solid, which
  11. customwas recrystallised from MeOH (300 ml) and H2O (100 ml)

Sources & evidence

ORD record
ord-90bcc32078c34d99b1a9ff0130aa7e97
Source dataset
uspto-grants-2001_11
Patent number
US06316468B1

Reaction notes

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