Methyl iodide → 2-[(2,3-Dihydro-1H-inden-2-yl)methylamino]acetamide

HRID 1952965Notes

Reaction equation

HRID 1952965 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][CH2:11][C:12]([NH2:14])=[O:13].[C:15](=O)([O-])[O-].[K+].[K+].CI>CO>[CH3:15][N:10]([CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)[CH2:11][C:12]([NH2:14])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10192617202844-10-8

Product 1

HCID 233020372-[(2,3-Dihydro-1H-inden-2-yl)methylamino]acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-indanylamino)acetamide (0.016 moles, 3.00 g) is dissolved in methanol (60 ml), and potassium carbonate (0.016 moles, 2.18 g) is added under stirring. Methyl iodide (0.028 moles, 4.14 g) is dropped therein at r.t. in 15 minutes. The mixture is reacted for 4 hours at r.t., then evaporated under vacuum. The resulting solid is taken up into water (100 ml), the aqueous solution is extracted with ethyl acetate (3×150 ml). The organic solution is dried over sodium sulfate, then evaporated under vacuum to obtain an oil which is chromatographed under medium pressure through silica gel (eluent chloroform:methanol=90:10) Yield: 1.31 g (40%)--m.p.=122-123° C.

Workup

  1. customThe mixture is reacted for 4 hours at r.t.
  2. customevaporated under vacuum
  3. extractionthe aqueous solution is extracted with ethyl acetate (3×150 ml)
  4. dry with materialThe organic solution is dried over sodium sulfate
  5. customevaporated under vacuum
  6. customto obtain an oil which
  7. customis chromatographed under medium pressure through silica gel (eluent chloroform:methanol=90:10) Yield: 1.31 g (40%)

Sources & evidence

ORD record
ord-081d2e55f36744369c3ccfba5aa1740e
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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