Dichloromethane → HCID 67047755, compound

HRID 890117Notes

Reaction equation

HRID 890117 reaction equation
C([O:5][C:6]1[C:7]([CH2:12][N:13]2[CH2:18][CH2:17][C@H:16]([OH:19])[C@H:15]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[CH2:14]2)=[N:8][CH:9]=[CH:10][N:11]=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][C@H:15]1[C@@H:16]([OH:19])[CH2:17][CH2:18][N:13]([CH2:12][C:7]2[C:6](=[O:5])[NH:11][CH:10]=[CH:9][N:8]=2)[CH2:14]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 67047325HCID 67047325, compound

Product 1

HCID 67047755HCID 67047755, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

After dissolving 198 mg of cis-1-(3-tert-butoxy-2-pyrazinylmethyl)-3-(2-fluorophenoxymethyl)piperidin-4-ol in 3 ml of ethyl acetate, 3 ml of 4N hydrogen chloride/ethyl acetate was added while stirring on ice. After 1 hour, aqueous sodium bicarbonate solution was added to the reaction solution and extraction was performed with dichloromethane. The extract was 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 (68 mg, 40% yield).

Workup

  1. additionwas added
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionDiethyl ether was added to the residue
  5. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-44d94a6f6246475f96fa35653db9ae2d
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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