Acetic Acid → HCID 9998314, compound

HRID 645897Notes

Reaction equation

HRID 645897 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[CH:24]=[CH:23]C(C#N)=[CH:19][C:18]=4[F:25])=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[C:28]([OH:31])(=[O:30])[CH3:29]>C(O)C.O>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[CH:24]=[CH:23][C:29]([C:28]([OH:31])=[O:30])=[CH:19][C:18]=4[F:25])=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 10337091HCID 10337091, compound

Product 1

HCID 9998314HCID 9998314, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-fluorobenzonitrile (E271) (150 mg, 0.45 mmol) was dissolved in a mixture of ethanol (1 ml) and water (1.5 ml), treated with sodium hydroxide (150 mg, 4.5 mmol) and heated at reflux for 2 hours. The reaction was then treated with acetic acid (0.39 ml, 6.75 mmol) and concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (2:18:80) to afford the title compound. MS (ES+) m/e 356 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography
  5. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (2:18:80)

Sources & evidence

ORD record
ord-74ee400dc2e04bcc82b77801e80f6e40
Source dataset
uspto-grants-2010_04
Patent number
US07704994B2

Reaction notes

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