Methanol → 7-(5-Methyl-isoxazol-3-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 33208Notes

Reaction equation

HRID 33208 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][C:14]([C:16]3[CH:20]=[C:19]([CH3:21])[O:18][N:17]=3)=[CH:15][C:8]=2[CH2:7][CH2:6]1)=O.C([O-])([O-])=O.[K+].[K+].CO>O>[CH3:21][C:19]1[O:18][N:17]=[C:16]([C:14]2[CH:13]=[CH:12][C:9]3[CH2:10][CH2:11][NH:5][CH2:6][CH2:7][C:8]=3[CH:15]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 23631175HCID 23631175, compound

Product 1

HCID 690161167-(5-Methyl-isoxazol-3-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-trifluoracetyl-7-(5-methyl-isoxazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine (7.1 g) and K2CO3 (12.1 g) in 1:1 methanol:water (400 ml) was heated at 50° C. for 1 h. The mixture was cooled, poured into water (500 ml) and extracted with dichloromethane. The combined organic layers were dried and evaporated in vacuo to give the title compound as a yellow oil (3.9 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with dichloromethane
  3. customThe combined organic layers were dried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-16677af7c12549128b85b568199e1c83
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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