Sodium Hydroxide → HCID 22248353, compound

HRID 914913Notes

Reaction equation

HRID 914913 reaction equation
Cl.C(OCC)(=O)C.C([O:12][C:13]1[C:14]([CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([CH:26]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])[C:27]#[N:28])[CH2:22][CH2:21]2)=[N:15][CH:16]=[CH:17][N:18]=1)(C)(C)C.[OH-].[Na+]>C(OCC)(=O)C>[F:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][CH:26]([CH:23]1[CH2:22][CH2:21][N:20]([CH2:19][C:14]2[C:13](=[O:12])[NH:18][CH:17]=[CH:16][N:15]=2)[CH2:25][CH2:24]1)[C:27]#[N:28]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 22248171HCID 22248171, compound

Product 1

HCID 22248353HCID 22248353, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

After adding 3 ml of 4N hydrogen chloride/ethyl acetate to 188 mg of 2-[1-(3-tert-butoxy-2-pyrazinylmethyl)piperidin-4-yl]-3-(2-fluorophenyl)propionitrile while cooling on ice, the mixture was stirred 1 hour. A 2N sodium hydroxide solution was added to the reaction solution for neutralization, and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Diethyl ether was added to the residue and the mixture was filtered to obtain the title compound (129 mg, 80% yield).

Workup

  1. temperaturewhile cooling on ice
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionDiethyl ether was added to the residue
  6. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-3d4a0a73476849da9f1d037ec009b4d8
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

Loading…