Water → HCID 54221552, compound

HRID 1590039Notes

Reaction equation

HRID 1590039 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([O:9][C:10](=[O:34])[NH:11][N:12]1[CH2:18][CH:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[C:16]2[CH:30]=[CH:31][CH:32]=[CH:33][C:15]=2[CH2:14][CH2:13]1)[CH3:8].S(OC)(OC)(=O)=O.O>O1CCCC1>[CH2:7]([O:9][C:10](=[O:34])[N:11]([CH3:1])[N:12]1[CH2:18][CH:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][CH:21]=2)[C:16]2[CH:30]=[CH:31][CH:32]=[CH:33][C:15]=2[CH2:14][CH2:13]1)[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 23665647Potassium tert-butoxideHCID 54532145HCID 54532145, compound

Product 1

HCID 54221552HCID 54221552, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium-t-butoxide (3 g) was added as a powder to an ice-cooled solution of N-[2,3,4,5-tetrahydro-1-(4-trifluoromethylphenoxy)3-benzazepin-3-yl]carbamic acid ethyl ester (8 g) in 100 ml tetrahydrofuran. After thirty minutes, a solution of dimethyl sulfate (3.1 g) in 25 ml tetrahydrofuran was slowly added. After one hour, the reaction mixture was stirred with water and extracted with ethyl acetate. The dried (anhydrous magnesium sulfate) organic layer was filtered and concentrated. The residue was triturated with ether to yield 6 g solid, mp 204°-205°. A 2 gram sample was recrystallized from acetonitrile to yield 1.6 g white crystals, mp 218°-219°.

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
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-d57c68a417034130a5e27d08000aba9f
Source dataset
uspto-grants-1993_04
Patent number
US05202319

Reaction notes

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