Dimethylamine → HCID 21836659, compound

HRID 1740217Notes

Reaction equation

HRID 1740217 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:21]=[C:22]=[O:23])=[CH:11][CH:10]=1.[CH3:24][NH:25][CH3:26]>CO>[OH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:21][C:22]([N:25]([CH3:26])[CH3:24])=[O:23])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 21836704HCID 21836704, compound

Product 1

HCID 21836659HCID 21836659, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the crude intermediate from Step A in 4 mL of methanol was treated with 4 mL of 40% aqueous dimethylamine. After stirring at room temperature for 15 minutes, the reaction mixture was evaporated under vacuum and the residue dissolved in 4 mL of methanol and treated with 1 mL of 10% methanolic p-toluenesulfonic acid. After 15 minutes at room temperature, the reaction mixture was treated with saturated aqueous sodium bicarbonate. The mixture was diluted with water then extracted with methylene chloride. The organic layer was dried and evaporated under vacuum; the residue was purified by preparative thin layer chromatography on silica gel, eluting with hexane/ethyl acetate (2:1) to afford 133 mg of product.

Workup

  1. customthe reaction mixture was evaporated under vacuum
  2. dissolutionthe residue dissolved in 4 mL of methanol
  3. additiontreated with 1 mL of 10% methanolic p-toluenesulfonic acid
  4. waitAfter 15 minutes at room temperature
  5. additionthe reaction mixture was treated with saturated aqueous sodium bicarbonate
  6. additionThe mixture was diluted with water
  7. extractionthen extracted with methylene chloride
  8. customThe organic layer was dried
  9. customevaporated under vacuum
  10. customthe residue was purified by preparative thin layer chromatography on silica gel
  11. washeluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-18e08fe0b62547c99d4a05f9ec6f1029
Source dataset
uspto-grants-1999_10
Patent number
US05968924

Reaction notes

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