Hydrochloric Acid → HCID 11749116, compound

HRID 1838233Notes

Reaction equation

HRID 1838233 reaction equation
B.C1COCC1.C1COCC1.[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:36])([F:35])[F:34])[CH:26]=2)[CH:21]([CH2:37][CH3:38])[C:20]1=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>CO>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:36])([F:34])[F:35])[CH:26]=2)[CH:21]([CH2:37][CH3:38])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuranHCID 18753337HCID 18753337, compound

Product 1

HCID 11749116HCID 11749116, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., 5 ml of 1 M borane-THF solution was added dropwise to 30 ml of anhydrous THF solution containing 1.47 g of 4-(4-benzyl-2-ethyl-3-oxopiperazin-1-yl)-2-trifluoromethylbenzonitrile synthesized in Reference Example 5-1, and the mixture was stirred for 4 hours. After addition of 10 ml of methanol and 38 ml of 1 N hydrochloric acid to the mixture with stirring, the reaction solution was evaporated under reduced pressure, the resulting residue was neutralized with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate, the organic layer was washed and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by a silica gel column chromatography, and 0.67 g of the title compound was obtained from hexane-ethyl acetate (5:1, v/v) eluate as yellow oily substance.

Workup

  1. customsynthesized in Reference Example 5-1
  2. stirringwith stirring
  3. customthe reaction solution was evaporated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed
  6. customdried
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-4153e57f628f4a999a524570b4cbc767
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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