Indole → N-(3-acetoxypropyl)-indole

HRID 399675Notes

Reaction equation

HRID 399675 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[C:12]([O:15][CH2:16][CH2:17][CH2:18]Br)(=[O:14])[CH3:13]>CN(C=O)C>[C:12]([O:15][CH2:16][CH2:17][CH2:18][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 122357751-Propanol, 3-bromo-, 1-acetate

Product 1

HCID 15163043N-(3-acetoxypropyl)-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
50 °C

Procedure

To a stirred 0° C. DMF (400 mL) suspension of NaH (60% in mineral oil, 0.705 moles, 28.2 g, 1.5 eq.) in a three-neck flask fitted with a reflux condenser and an addition funnel was added a DMF (150 mL) solution of indole (55 g, 0.47 moles) dropwise. After 30-60 minutes, a DMF (50 mL) solution of the alkyl halide, 3-bromopropyl acetate (170 g, 0.94 moles) was added. The reaction was heated at 50° C. for 6 hours and then allowed to stir at room temperature for 5-15 hours.

Workup

  1. customTo a stirred 0° C
  2. customfitted with a reflux condenser and an addition funnel

Sources & evidence

ORD record
ord-6c6f410bde174ef9a30951ae6fcff4f4
Source dataset
uspto-grants-1998_10
Patent number
US05821365

Reaction notes

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