1-Benzyl-4-piperidone → HCID 57474457, compound

HRID 552935Notes

Reaction equation

HRID 552935 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].N1CCCC1.[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>C(O)C>[CH2:18]([N:25]1[CH2:26][CH:27]=[C:28]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][CH:8]=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 192201-Benzyl-4-piperidoneHCID 225235-NitroindoleHCID 31268Pyrrolidine

Product 1

HCID 57474457HCID 57474457, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-nitroindole (38) (1.0 g, 6.167 mmol) in dry ethanol (20 mL) was treated with pyrrolidine (1.54 mL, 18.501 mmol), N-benzyl-4-piperidone (2.2 mL, 12.3 mmol) at room temperature and the resulting solution was refluxed for 4 days. The reaction was brought to room temperature and solvent was evaporated. The crude product was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95) to obtain compound 71 (0.925 g, 45%) as a solid. mp 168-170° C.; 1H NMR (DMSO-d6) δ 2.51-2.55 (m, 2H), 2.66 (t, 2H, J=5.4 Hz), 3.12-3.18 (m, 2H), 3.60 (s, 2H), 6.17 (s, 1H), 7.23-7.38 (m, 5H), 7.55 (d, 1H, J=9.0 Hz), 7.65 (s, 1H), 8.01 (dd, 1H, J=2.1, 8.7 Hz), 8.68 (d, 1H, J=2.1 Hz), 11.87 (s, 1H); ESI-MS m/z (%): 334 (M+, 100).

Workup

  1. temperaturethe resulting solution was refluxed for 4 days
  2. customwas brought to room temperature
  3. customsolvent was evaporated
  4. customThe crude product was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-939e8aa891ff491f8a7e6d959b3a2395
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

Loading…