Hydrochloric Acid → HCID 19786539, compound

HRID 1646715Notes

Reaction equation

HRID 1646715 reaction equation
CN([CH2:4][N:5]([CH3:7])[CH3:6])C.FC(F)(F)C(O)=O.[C:15]1([C:21]2[C:25]3[C:26](=[O:30])[CH2:27][CH2:28][CH2:29][C:24]=3[O:23][N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[ClH:31]>>[ClH:31].[CH3:7][N:5]([CH2:4][CH:27]1[C:26](=[O:30])[C:25]2[C:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:22][O:23][C:24]=2[CH2:29][CH2:28]1)[CH3:6]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6422Trifluoroacetic acidHCID 12344070HCID 12344070, compound

Product 1

HCID 19786539HCID 19786539, compound

Conditions

Temperature
-10 °C

Procedure

Bis-dimethylaminomethane (0.51 g) was added to 2.5 ml of trifluoroacetic acid which had been previously chilled to -10° C. 6,7-Dihydro-3-phenyl-1,2-benzisoxazol-4(5H)-one (1.0 g) was then added and the reaction was warmed for 1 hour at 100° C. and then allowed to stand an additional 2 days at room temperature. The reaction mixture was poured into 5% HCl and washed with ether, after which the aqueous phase was treated with solid sodium bicarbonate until basic. Extraction with ether followed by drying and concentration gave an oil. The hydrochloride was formed in ethereal HCl and was recrystallized from dichloromethane/ether to give 0.95 g of 6,7-dihydro-5-dimethylaminomethyl-3-phenyl-1,2-benzisoxazol-4(5H)-one hydrochloride, m.p. 178°-180° C.

Workup

  1. temperaturethe reaction was warmed for 1 hour at 100° C.
  2. washwashed with ether
  3. additionafter which the aqueous phase was treated with solid sodium bicarbonate until basic
  4. extractionExtraction with ether
  5. customby drying
  6. concentrationconcentration
  7. customgave an oil

Sources & evidence

ORD record
ord-146d0cbf56d04b52959c98c6542a93d1
Source dataset
uspto-grants-1993_01
Patent number
US05180834

Reaction notes

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