Water → HCID 19769440, compound

HRID 1590041Notes

Reaction equation

HRID 1590041 reaction equation
[CH3:1]C(C)([O-])C.[K+].[F:7][C:8]([F:35])([F:34])[C:9]1[CH:33]=[CH:32][C:12]([O:13][CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][N:16]([NH:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH2:15]2)=[CH:11][CH:10]=1.S(OC)(OC)(=O)=O.O>O1CCCC1>[CH3:1][N:25]([N:16]1[CH2:15][CH:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([C:8]([F:34])([F:7])[F:35])=[CH:33][CH:32]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17]1)[C:26](=[O:31])[C:27]([F:28])([F:29])[F:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 19769443HCID 19769443, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19769440HCID 19769440, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium-t-butoxide (1.4 g) was added as a powder to an ice-cooled solution of N-[2,3,4,5-tetrahydro-1-(4-trifluoromethylphenoxy)-1H-3-benzazepin-3-yl]-trifluoroacet amide (4 g) in 100 mL tetrahydrofuran. After thirty minutes, dimethyl sulfate (1.5 g) was added. After warming to ambient temperature, the reaction mixture was stirred with water and extracted with ethyl acetate. The dried (anhydrous magnesium sulfate) organic layer was filtered and concentrated to 4.1 g solid, mp 210°-212°. A 2.5 g portion was recrystallized from acetonitrile to yield 1.6 g white crystals, mp 216°-218°.

Workup

  1. waitAfter thirty minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe dried (anhydrous magnesium sulfate) organic layer
  4. filtrationwas filtered
  5. concentrationconcentrated to 4.1 g solid, mp 210°-212°
  6. customA 2.5 g portion was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-0571d32facb141fbb3ce8c1b0deedf60
Source dataset
uspto-grants-1993_04
Patent number
US05202319

Reaction notes

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