Potassium Carbonate → Ethyl 4-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]butanoate

HRID 641502Notes

Reaction equation

HRID 641502 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:10]1([N:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:17]=3[CH2:16][CH2:15]2)[CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH:10]1([N:14]2[CH2:15][CH2:16][C:17]3[CH:24]=[CH:23][C:22]([O:25][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:21][C:18]=3[CH2:19][CH2:20]2)[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 100820813-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

Product 1

HCID 9996814Ethyl 4-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]butanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Ethyl 4-bromobutyrate (2 ml, 13.8 mmol) was added to a stirred solution of 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E3) (2.00 g, 9.2 mmol) and potassium carbonate (3.8 g, 27.6 mmol) in 2-butanone (50 ml). After stirring at reflux for 24 hours, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The resulting crude material was purified by column chromatography eluting with a mixture of methanol:dichloromethane (5:95) to afford the title compound (E167a). MS (ES+) m/e 332 [M+H]+

Workup

  1. temperatureat reflux for 24 hours
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude material was purified by column chromatography
  5. washeluting with a mixture of methanol:dichloromethane (5:95)

Sources & evidence

ORD record
ord-7666345dcb3a47748f86b409b07df5a5
Source dataset
uspto-grants-2010_04
Patent number
US07696193B2

Reaction notes

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