Hydrochloric Acid → 4-({[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}oxy)benzoic acid

HRID 1691696Notes

Reaction equation

HRID 1691696 reaction equation
[C:1]1([C@H:11]([NH:13][CH2:14][CH:15]2[CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][CH2:18][N:17]([C:27]([O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]([O:38]C)=[O:37])=[CH:32][CH:31]=3)=[O:28])[CH2:16]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1COCC1.[OH-].[Na+].Cl>CO>[C:1]1([C@H:11]([NH:13][CH2:14][CH:15]2[CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][CH2:18][N:17]([C:27]([O:29][C:30]3[CH:31]=[CH:32][C:33]([C:36]([OH:38])=[O:37])=[CH:34][CH:35]=3)=[O:28])[CH2:16]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 591787354-(methoxycarbonyl)phenyl 3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidine-1-carboxylate

Product 1

HCID 591786744-({[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}oxy)benzoic acidYield 29.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 232 mg of 4-(methoxycarbonyl)phenyl 3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidine-1-carboxylate were added 6.0 mL of THF, 3.0 mL of methanol, and 3.0 mL of a 1 M aqueous sodium hydroxide solution, followed by stirring at room temperature overnight. After neutralizing by addition of 3.0 mL of 1 M hydrochloric acid, the reaction mixture was concentrated under reduced pressure. To the residue was added water, followed by extraction with chloroform, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform-methanol). This was dissolved in a small amount of chloroform, and hexane was added thereto. Then, the precipitate was isolated by filtration, and dried under reduced pressure at 50° C. to obtain 66 mg of 4-({[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]carbonyl}oxy)benzoic acid as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added water
  3. extractionfollowed by extraction with chloroform
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform-methanol)
  8. dissolutionThis was dissolved in a small amount of chloroform, and hexane
  9. additionwas added
  10. customThen, the precipitate was isolated by filtration
  11. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-5d2daa4dea384e89ae30112166bebf47
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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