Acetic Acid → 1-[(5-Chloro-2-methoxy-3-pyridinyl)methyl]-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidine

HRID 1837762Notes

Reaction equation

HRID 1837762 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1/[CH:19]=[CH:20]/[CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][N:24]2[CH2:25][CH2:26][CH:21](/[CH:20]=[CH:19]/[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[F:12])[CH2:22][CH2:23]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 135677575-Chloro-2-methoxynicotinaldehydeHCID 22248269(E)-4-[2-(2-fluorophenyl)vinyl]piperidine

Product 1

HCID 226785031-[(5-Chloro-2-methoxy-3-pyridinyl)methyl]-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidineYield 58.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

200 mg of 5-chloro-2-methoxy-3-pyridinecarboxaldehyde and 263 mg of 4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidine were dissolved in 5 ml of 1,2-dichloroethane. To the mixture were added 0.09 ml of acetic acid and 339 mg of sodium triacetoxyborohydride, followed by stirring at room temperature for 2.5 hours. The reaction solution was filtered through NH-form silica gel, and the filtrate was evaporated. Ethyl acetate was added to the residue, and the mixture was filtered through alumina, and the filtrate was evaporated. The crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to give 245 mg of the title compound as a colorless oil.

Workup

  1. filtrationThe reaction solution was filtered through NH-form silica gel
  2. customthe filtrate was evaporated
  3. additionEthyl acetate was added to the residue
  4. filtrationthe mixture was filtered through alumina
  5. customthe filtrate was evaporated
  6. customThe crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-dacb3c9796b5459fa1c09729958be716
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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