Dimethylamine → HCID 70393278, compound

HRID 2291775Notes

Reaction equation

HRID 2291775 reaction equation
[CH3:1][NH:2][CH3:3].[C:4]([OH:11])(=[O:10])/[CH:5]=[CH:6]\[C:7]([OH:9])=[O:8].NC[C:14]([NH:16][C:17]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:25]([F:28])([F:27])[F:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15].[C:35](O)(=O)/C=C\C(O)=O>CO>[C:4]([OH:11])(=[O:10])/[CH:5]=[CH:6]\[C:7]([OH:9])=[O:8].[CH3:1][N:2]([CH3:35])[CH2:3][C:14]([NH:16][C:17]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:25]([F:28])([F:27])[F:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 444266Maleic AcidHCID 70393299HCID 70393299, compound

Product 1

HCID 70393278HCID 70393278, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of dimethylamine (25 ml, 0.38 mol) in 150 ml of methanol at 0° C. under nitrogen, was added 2-chloro-N-[1,2-diphenyl-1-(trifluoromethyl)ethyl]acetamide (from Example 1) (7.0 g, 0.020 mol). The mixture was allowed to slowly warm to ambient temperature and stirred for 48 hours. The solvent was evaporated and the residue was dissolved in 150 ml of chloroform and 150 ml of water. The aqueous solution was basified to a pH of 10 with 50% NaOH. The phases were separated, the aqueous phase extracted with chloroform (2×75 ml) and the combined organic phases were washed with brine (75 ml), dried and evaporated to a dark oil, 7.2 g. This oil was purified by chromatograhy on a Prep 500 HPLC on silica gel, eluting with 10% ethylacetate/hexane. Pure fractions were combined and evaporated to 4.0 g of an oil. This oil was dissolved in 125 ml of methanol and treated with maleic acid (1.3 g, 0.012 mol) at reflux. The solution was concentrated to a volume of 75 ml. The crystalline salt which formed, was vacuum dried to give 3.61 g of 2-(dimethylamino)-N-[1,2-diphenyl-1-(trifluoromethyl)ethyl]acetamide maleate as a white solid, mp 213°-215° C.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 150 ml of chloroform
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted with chloroform (2×75 ml)
  5. washthe combined organic phases were washed with brine (75 ml)
  6. customdried
  7. customevaporated to a dark oil, 7.2 g
  8. customThis oil was purified by chromatograhy on a Prep 500 HPLC on silica gel
  9. washeluting with 10% ethylacetate/hexane
  10. customevaporated to 4.0 g of an oil
  11. dissolutionThis oil was dissolved in 125 ml of methanol
  12. temperatureat reflux
  13. concentrationThe solution was concentrated to a volume of 75 ml
  14. customThe crystalline salt which formed
  15. customdried

Sources & evidence

ORD record
ord-7e2eb44824864308a577d8c5bdc923e3
Source dataset
uspto-grants-1989_01
Patent number
US04798687

Reaction notes

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