Methyl iodide → HCID 54136909, compound

HRID 330192Notes

Reaction equation

HRID 330192 reaction equation
[CH2:1]([NH:5][C:6](=[O:17])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].I[CH3:21]>CN(C)C=O>[CH2:1]([NH:5][C:6](=[O:17])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:21])[CH:12]=[CH:11]2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53914725HCID 53914725, compound

Product 1

HCID 54136909HCID 54136909, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-butylindole-5-acetamide (1.0 g) in dimethylformamide (15 ml) was added to a slurry of sodium hydride (0.11 g) in dimethylformamide (7 ml) at 0° under a nitrogen atmosphere, stirred for 1 hr at 0° and treated with iodomethane (0.3 ml). The reaction was quenched with saturated ammonium chloride solution and diluted with water. The precipitate that formed was collected by filtration, washed with water, and dried under vaccum to give N-butyl-1-methyl-indole-5-acetamide (0.46 g, 43%) as a pale yellow powder: NMR (250 MHz, CDCl3): 0.84(t, 3H, N(CH2)3CH3), 1.38-1.17(m, 4H, NCH2 (CH2)2), 3.16(q, 2H, NCH2), 3.67(s, 2H, ArCH2), 3.80(s, 3H, NCH3), 5.43(br, 1H, NH), 6.45(d, 1H, H2 -indole).

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. additiondiluted with water
  3. customThe precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried under vaccum

Sources & evidence

ORD record
ord-3bed9257a9574a7eaf0444791fd23cbd
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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