Dimethylamine → HCID 15055764, compound

HRID 2351549Notes

Reaction equation

HRID 2351549 reaction equation
[CH3:1][NH:2][CH3:3].Cl[CH2:5][C:6]([N:8]([CH3:24])[C:9]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:7].C(Cl)(Cl)Cl>CO>[C:18]1([C:9]2([N:8]([CH3:24])[C:6](=[O:7])[CH2:5][N:2]([CH3:3])[CH3:1])[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 6212ChloroformHCID 19846175HCID 19846175, compound

Product 1

HCID 15055764HCID 15055764, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of dimethylamine (30 mL, 0.45 mol) in methanol (150 mL) at 0° C. under nitrogen were added 2-chloro-N-methyl-N-(2,3-dihydro-2-phenyl-1H-inden-2-yl)acetamide (8.0 g, 0.027 mol) and chloroform (110 mL). The mixture was stirred at ambient temperature for 60 hours. The solvents were evaporated, the residue was dissolved in chloroform (250 mL) and 5% NaOH (250 mL), and the phases were separated. The aqueous phase was extracted with chloroform (3×200 mL). The combined chloroform extracts were washed with brine (200 mL), dried over magnesium sulfate and the solvent evaporated. The residual solid (8.1 g) was dissolved in ethanol (175 mL) and acidified with HCl gas. The solid which formed was collected by filtration and vacuum dried at 65° C. for 48 hours to provide 8.0 g of N-(2,3-dihydro-2-phenyl-1H-inden-2-yl)-N-methyl-2(dimethylamino)acetamide, mp 244°-245° C.

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in chloroform (250 mL)
  3. custom5% NaOH (250 mL), and the phases were separated
  4. extractionThe aqueous phase was extracted with chloroform (3×200 mL)
  5. washThe combined chloroform extracts were washed with brine (200 mL)
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent evaporated
  8. dissolutionThe residual solid (8.1 g) was dissolved in ethanol (175 mL)
  9. customThe solid which formed
  10. filtrationwas collected by filtration and vacuum
  11. customdried at 65° C. for 48 hours

Sources & evidence

ORD record
ord-8511bf899f4a43889ecbd68e018a0f36
Source dataset
uspto-grants-1989_10
Patent number
US04873241

Reaction notes

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