5-Nitroindole → 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole

HRID 2043489Notes

Reaction equation

HRID 2043489 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.[CH3:18][N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1>C(O)C>[CH3:18][N:19]1[CH2:20][CH:21]=[C:22]([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)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 225235-NitroindoleHCID 31268PyrrolidineHCID 740491-Methyl-4-piperidone

Product 1

HCID 113343733-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indoleYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-nitroindole (38) (0.5 g, 3.083 mmol) in dry ethanol (5 mL) was treated with pyrrolidine (0.77 mL, 9.250 mmol), N-methyl-4-piperidone (0.75 mL, 6.167 mmol) at room temperature. The resulting solution was refluxed for 2 days. The reaction was brought to room temperature, the solid was filtered off, washed with ethanol (2×5 mL) and dried to obtain compound (39) (0.591 g, 75%). Solid decomposed at 215° C.; 1H NMR (DMSO-d6) δ 2.29 (s, 3H), 2.50-2.59 (m, 4H), 3.06-3.08 (m, 2H), 6.17 (br s, 1H), 7.55 (d, 1H, J=9.0 Hz), 7.66 (s, 1H), 8.01 (dd, 1H, J=2.1, 9.0 Hz), 8.68 (d, 1H, J=2.1 Hz), 11.86 (brs, 1H).

Workup

  1. temperatureThe resulting solution was refluxed for 2 days
  2. customwas brought to room temperature
  3. filtrationthe solid was filtered off
  4. washwashed with ethanol (2×5 mL)
  5. customdried

Sources & evidence

ORD record
ord-dfd7c785f27045e1a8db46488bc904f9
Source dataset
uspto-grants-2013_11
Patent number
US08586620B2

Reaction notes

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