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

HRID 735050Notes

Reaction equation

HRID 735050 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 16.22 g (0.1 mol) of 5-nitroindole, 35 g (0.205 mol) of 1-(2-chloroethyl)pyrrolidine hydrochloride, and 51 g (0.369 mol) of potassium carbonate in 500 mL of DMF is stirred for 48 hours at ambient temperature and then filtered. The filtrate is evaporated down, the residue dissolved in dichloromethane and dried over sodium sulfate. The desiccant is filtered off and the filtrate is evaporated down. Yield: 25 g (96.3% of theory); C14H17N3O2 (M=259.31); calc.: molecular ion peak (M+H)+: 260; found: molecular ion peak (M+H)+: 260; Rf value: 0.65 (silica gel, dichloromethane/methanol/ammonia (90:10:1)).

Workup

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

Sources & evidence

ORD record
ord-a396d7ab3dd0446fa900d1a867535b61
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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