Isopropyl iodide → 1-(1-Methylethyl)-6-(4-methyl-1-piperazinyl)-1H-indole

HRID 2084063Notes

Reaction equation

HRID 2084063 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH:12]=[CH:13][NH:14]3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[H-].[Na+].I[CH:26]([CH3:28])[CH3:27]>C1(C)C=CC=CC=1.ClCCl.CN(C=O)C>[CH:26]([N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[CH:16]=2)[CH:12]=[CH:13]1)([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 98157856-(4-methylpiperazin-1-yl)-1H-indole

Product 1

HCID 97951031-(1-Methylethyl)-6-(4-methyl-1-piperazinyl)-1H-indoleYield 83%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 6-(4-methylpiperazinyl)-indole (8.3 mg, 0.386 mmol), K2CO3 (21 mg, 0.154 mmol), NaH (3 mg, 0.125 mmol), DMF (0.1 ml) and 2-iodopropane (26.3 μl, 0.154 mmol) in 0.5 ml of toluene was heated to 90-100° C. for 1 hr. After cooling, dichloromethane was added and the mixture passed a silica gel column, eluting with 1% 2M ammonia/methanol in dichloromethane, to give the title compound (8.2 mg, 83% yield).

Workup

  1. temperatureAfter cooling
  2. washeluting with 1% 2M ammonia/methanol in dichloromethane

Sources & evidence

ORD record
ord-06bd8f7730524473a300b38dcfca9523
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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