Phosphoric Acid → HCID 59508093, compound

HRID 1958647Notes

Reaction equation

HRID 1958647 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:7][CH:6]=[CH:5][N:4]=1.[CH2:18]([N:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.OP(O)(O)=O>C(O)(=O)C>[CH2:18]([N:25]1[CH2:26][CH:27]=[C:28]([C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:29][CH2:30]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 192201-Benzyl-4-piperidoneHCID 59508107HCID 59508107, compound

Product 1

HCID 59508093HCID 59508093, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(2-methoxy-pyridin-3-yl)-1H-indole (0.43 g, 1.94 mmol) in acetic acid (12 ml) was added 1-benzyl-piperidin-4-one (1.10 g, 5.82 mmol) and H3PO4 (4 ml). The reaction was stirred at 100° C. for 3 h. The reaction was cooled to room temperature and poured into ice/NH4OH and filtered. The solid was washed with water and dissolved in dichloromethane. The crude product was purified by flash column chromatography (SiO2, 66% EtOAc in hexanes). The desired product was obtained as a tan solid (0.64 g, 83%). LCMS: 396.75 [M+H].

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. washThe solid was washed with water
  4. dissolutiondissolved in dichloromethane
  5. customThe crude product was purified by flash column chromatography (SiO2, 66% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a40754a4714046f4a9ae93e2dacf2e0c
Source dataset
uspto-grants-2013_04
Patent number
US08410144B2

Reaction notes

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