HCID 22126486, compound → HCID 22128104, compound

HRID 1004962Notes

Reaction equation

HRID 1004962 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OCC(Cl)(Cl)Cl)=O)[CH2:10][CH:9]2[O:22][CH2:23][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)=[CH:4][CH:3]=1>C(O)(=O)C.O.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[O:22][CH2:23][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 22126486HCID 22126486, compound

Product 1

HCID 22128104HCID 22128104, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A suspension of 0.420 g (0.8 mmol) of 2,2,2-trichloroethyl 4-(4-chloro-phenyl)-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate and 300 mg of zinc in 10 ml of acetic acid was stirred at room temperature for 12 hours. The reaction solution was diluted with 40 ml of water and extracted four times with 30 ml of methylene chloride. The organic phase was washed twice with 40 ml of 1N sodium hydroxide solution each time, dried over sodium sulphate, filtered and evaporated. The residue was chromatographed on silica gel using a 9:1 mixture of methylene chloride and methanol as the eluent. There was obtained 0.210 g (74% of theory) of (3RS,4RS)-4-(4-chloro-phenyl)-3-(naphthalen-2-ylmethoxy)-piperidine, MS: 210 (M-C11H9)+, which was converted into the hydrochloride of m.p. 159-161° C. (dec.) with a solution of hydrogen chloride in methanol.

Workup

  1. extractionextracted four times with 30 ml of methylene chloride
  2. washThe organic phase was washed twice with 40 ml of 1N sodium hydroxide solution each time
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel using
  7. additiona 9:1 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-96c200bcbd5647f0b430a7de19a86b38
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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