HCID 18001190, compound → 4-(Naphthalen-1-yl)piperidine--hydrogen chloride (1/1)

HRID 478196Notes

Reaction equation

HRID 478196 reaction equation
[C:1]1([CH:11]2[CH2:16][CH2:15][N:14](C(OCC(Cl)(Cl)[Cl:22])=O)[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Zn]>[ClH:22].[C:1]1([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 18001190HCID 18001190, compound

Product 1

HCID 180011874-(Naphthalen-1-yl)piperidine--hydrogen chloride (1/1)Yield 73.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4-(1-naphthyl)-1-(2,2,2-trichloroethoxycarbonyl)piperidine (0.85 g, 2.2 mmol) and a powdered zinc (0.80 g, 1.2 mmol) in acetic acid (22 mL) was stirred at room temperature overnight. After filtrating the reaction mixture through Celite, the filtrate was concentrated, and a saturated aqueous sodium hydrogencarbonate was then added to pH of 10, and the resulting mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the chloroform layer was concentrated, and the resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; chloroform) to afford a free form of the title compound (0.4 g) as a pale yellow oil. After adding hydrochloric acid/methanol, a solution of the free form (0.4 g) in methanol was cooled to afford the title compound (0.36 g, yield: 66%) as white crystals.

Workup

  1. filtrationAfter filtrating the reaction mixture through Celite
  2. concentrationthe filtrate was concentrated
  3. additiona saturated aqueous sodium hydrogencarbonate was then added to pH of 10
  4. extractionthe resulting mixture was extracted with chloroform
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. concentrationthe chloroform layer was concentrated
  7. customthe resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; chloroform)

Sources & evidence

ORD record
ord-035e344b88324051b062e26b402b0f93
Source dataset
uspto-grants-2003_11
Patent number
US06642228B1

Reaction notes

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