Potassium Carbonate → 5-nitro-1-(2-pyrrolidin-1-ylethyl)-1H-indole

HRID 1820865Notes

Reaction equation

HRID 1820865 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].Cl.Cl[CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 225235-NitroindoleHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 114026955-nitro-1-(2-pyrrolidin-1-ylethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction mixture of 16.2 g (100 mmol) of 5-nitroindole, 35.0 g (206 mmol) of 1-(2-chloroethyl)pyrrolidine hydrochloride, and 51.0 g (369 mmol) of potassium carbonate in 500 mL of DMF is stirred for 48 hours at ambient temperature and then filtered. The filtrate is evaporated down, and the residue is dissolved in dichloromethane and dried over sodium sulfate. The drying agent is filtered off and the filtrate evaporated down. Yield: 25 g (96% of theory); Rf value: 0.65 (silica gel, dichloromethane/methanol/ammonia=9:1:0.1); C14H17N3O2; EII mass spectrum: m/z=260 [M+H]+.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated down
  3. dissolutionthe residue is dissolved in dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationThe drying agent is filtered off
  6. customthe filtrate evaporated down

Sources & evidence

ORD record
ord-0365bccdb02e40e68266046c2c878910
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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