Succinic anhydride → HCID 59324177, compound

HRID 508121Notes

Reaction equation

HRID 508121 reaction equation
[F:1][C:2]([F:8])([F:7])[C:3]1([NH2:6])[CH2:5][CH2:4]1.C(N(C(C)C)CC)(C)C.[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1>O1CCOCC1>[O:24]=[C:18]([NH:6][C:3]1([C:2]([F:8])([F:7])[F:1])[CH2:5][CH2:4]1)[CH2:19][CH2:20][C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 81531DiisopropylethylamineHCID 116511971-(Trifluoromethyl)cyclopropanamine

Product 1

HCID 59324177HCID 59324177, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

Slowly, 800.7 mg (4.96 mmol) of 1-(trifluoromethyl)cyclopropanamine and 0.85 ml (4.96 mmol) of diisopropylethylamine were added to a solution of 496 mg (4.96 mmol) of succinic anhydride in 10 ml of dioxane, with ice-cooling (10° C.). Stirring was continued for 20 min at room temperature, and the mixture was allowed to stand overnight at this temperature. Again, stirring was continued for 20 min at 80° C., the mixture was allowed to cool to room temperature, and the solution was concentrated. Repeatedly, the solution was washed alternately with ethyl acetate and with water. The combined organic phases were dried and concentrated. This gave 815.8 mg (73% of theory) of the desired compound.

Workup

  1. waitto stand overnight at this temperature
  2. stirringAgain, stirring
  3. waitwas continued for 20 min at 80° C.
  4. temperatureto cool to room temperature
  5. concentrationthe solution was concentrated
  6. washRepeatedly, the solution was washed alternately with ethyl acetate and with water
  7. customThe combined organic phases were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a35ca9a1533c4bfa8b56a7f8e3bdef7b
Source dataset
uspto-grants-2015_08
Patent number
US09095140B2

Reaction notes

Loading…