Potassium Iodide → N-benzyl-N-methyl-1-(1-(4-nitrobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxamide

HRID 83641

Reaction equation

HRID 83641 reaction equation
[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1.[I-].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)[C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 74824-Nitrobenzyl chlorideHCID 24758Sodium hydrideHCID 66571403N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

Product 1

HCID 66571462N-benzyl-N-methyl-1-(1-(4-nitrobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (50 mg, 0.133 mmol) was added to a suspension of sodium hydride (7.99 mg, 0.200 mmol) in DMF (Volume: 2 ml). The reaction was allowed to stir for 10 minutes at 60° C. 1-(chloromethyl)-4-nitrobenzene (45.7 mg, 0.266 mmol) and potassium iodide (44.2 mg, 0.266 mmol) were added and the reaction was stirred overnight at 60° C. The reaction was diluted with water and ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution. It was dried over magnesium sulfate, filtered and concentrated. The crude material was purified using 40-100% ethyl acetate:hexanes to afford the product as a white solid. (Yield: 11 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.20-8.12, 7.70-7.62, 7.55, 7.43-7.08, 6.81-6.75, 5.71-5.61, 4.62, 4.56-3.95, 3.21-2.85, 2.74, 1.81-1.13

Workup

  1. stirringthe reaction was stirred overnight at 60° C
  2. washThe organic layer was washed with water and saturated sodium chloride solution
  3. dry with materialIt was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified

Sources & evidence

ORD record
ord-7cb58c9091794a659a738e5a2395369a
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Linked notes

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