Triethylamine → 4-(3-Fluoro-4-methoxy-phenyl)-1-methanesulfonyl-1,2,3,6-tetrahydro-pyridine

HRID 222586Notes

Reaction equation

HRID 222586 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[F:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:16][CH2:15][N:14]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 668652484-(3-Fluoro-4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 668649704-(3-Fluoro-4-methoxy-phenyl)-1-methanesulfonyl-1,2,3,6-tetrahydro-pyridineYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Fluoro-4-methoxy-phenyl)-1,2,3,6-tetrahydro-pyridine hydrochloride salt (462.00 mg, 1.90 mmol) is suspended in dichloromethane (10 mL). Triethylamine (479.58 mg, 660.57 μL, 4.74 mmol) and methanesulfonyl chloride (260.59 mg, 176.07 μL, 2.27 mmol) are added and the reaction is capped and stirred at room temperature for 16 h. The reaction is partitioned between dichloromethane and water. The aqueous layer is extracted with dichloromethane. The combined organic layers are washed with brine, dried over magnesium sulfate, filtered, and concentrated to dryness. The crude material is purified by chromatography using a 5 g silica gel cartridge eluting with dichloromethane to provide 349 mg of the title compound as a white solid. MS (m/z) 286 (M+1).

Workup

  1. customthe reaction is capped
  2. customThe reaction is partitioned between dichloromethane and water
  3. extractionThe aqueous layer is extracted with dichloromethane
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude material is purified by chromatography
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-8fcc45da08c948859ba8a7213454bbc7
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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