Dichloromethane → HCID 22248589, compound

HRID 914876Notes

Reaction equation

HRID 914876 reaction equation
C([O:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[CH2:15]2)[N:7]=1)(C)(C)C.C(=O)(O)[O-].[Na+].ClCCl>C(OCC)(=O)C.Cl.C(OCC)(=O)C>[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[O:21][CH2:20][CH:16]1[CH2:17][CH2:18][CH2:19][N:14]([CH2:13][CH2:12][C:8]2[NH:7][C:6](=[O:5])[CH:11]=[N:10][CH:9]=2)[CH2:15]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 22248150HCID 22248150, compound

Product 1

HCID 22248589HCID 22248589, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

After dissolving 160 mg of 2-tert-butoxy-6-[2-[3-(2-fluorophenoxymethyl)piperidino]ethyl]pyrazine in 2 ml of ethyl acetate, 2 ml of 4N hydrogen chloride/ethyl acetate was added, and the mixture was allowed to stand at room temperature for 30 minutes. Aqueous sodium bicarbonate solution was added to the reaction solution and extraction was performed with dichloromethane. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, active carbon was added, and the mixture was filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (108 mg, 79% yield).

Workup

  1. additionwas added
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. additionactive carbon was added
  6. filtrationthe mixture was filtered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a84abd85f444f8a9e0da6f833b64ceb
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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