Water → HCID 23298443, compound

HRID 2393548Notes

Reaction equation

HRID 2393548 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8]2)([O-:4])=[O:3].[C:22](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[ClH:1].[N+:2]([C:5]1[CH:13]=[C:12]2[C:8](=[CH:7][CH:6]=1)[CH:9]([NH:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:10]([CH3:22])[CH2:11]2)([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23298424HCID 23298424, compound

Product 1

HCID 23298443HCID 23298443, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-nitro-2-(phenylmethyl)aminoindane hydrochloride (2.29 g, 7.52 mmol) in DMF (100 ml) was added potassium carbonate (2.60 g, 18.80 mmol) followed by methyl iodide (0.47 ml, 7.52 mmol). The mixture was warmed to room temperature, stirred for 16 hr, dumped into water (400 ml), and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water, dried over magnesium sulfate, filtered through a small plug of silica gel and reduced to a syrup. The titled compound was isolated as the hydrochloride salt: (1.08 g, 45%); m.p. dec 280° C.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered through a small plug of silica gel

Sources & evidence

ORD record
ord-639bb881eca64227b3afa95206b3f3eb
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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