N,N,N',N'-Tetramethylmethanediamine → HCID 13756068, compound

HRID 1249409Notes

Reaction equation

HRID 1249409 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH3:17]N(CN(C)C)C>FC(F)(F)C(O)=O>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[C:13](=[CH2:17])[CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

4

Reactant 2

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13756068HCID 13756068, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In 25 ml of trifluoroacetic acid cooled in ice was dissolved 5.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one. To the solution was added dropwise 6.70 ml (2.09 eq) of bisdimethylaminomethane over 5 minutes and thereafter the mixture was maintained at 90°-100° C. for 5 hours during which the starting material was converted to a mixture of intermediate and exo-methylene products. The reaction mixture was poured into ice/NaOH to make it basic and the precipitate was extracted with several portions of 5:1 dichloromethane/MeOH. The combined extracts were evaporated to a residue. The residue was refluxed in toluene for 5 hours during which the intermediate was converted to the end product. The reaction mixture was evaporated to a residue which was purified by chromatography on silica gel (EtOAc) to yield about 2 g of a solid. This was recrystallized from dichloromethane/EtOAc to yield 1.79 g (34%) of product as a solid, melting point 192°-193° C.

Workup

  1. temperaturethe mixture was maintained at 90°-100° C. for 5 hours during which the starting material
  2. additionwas converted to a mixture of intermediate and exo-methylene products
  3. extractionthe precipitate was extracted with several portions of 5:1 dichloromethane/MeOH
  4. customThe combined extracts were evaporated to a residue
  5. temperatureThe residue was refluxed in toluene for 5 hours during which the intermediate
  6. customThe reaction mixture was evaporated to a residue which
  7. customwas purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-e4d0fd21cf8f4f7fb2591e9ea58744ce
Source dataset
uspto-grants-1986_12
Patent number
US04631286

Reaction notes

Loading…