Pyridine → HCID 58266521, compound

HRID 1505888Notes

Reaction equation

HRID 1505888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:16])[CH:5]=[C:6]([Cl:15])[C:7]=1[CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.N1C=CC=CC=1.[F:23][C:24]([F:30])([F:29])[S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([O:16][S:25]([C:24]([F:30])([F:29])[F:23])(=[O:27])=[O:26])[CH:5]=[C:6]([Cl:15])[C:7]=1[CH2:8][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 79000Trifluoromethanesulfonyl chlorideHCID 582665303,5-Dichloro-4-piperidin-1-ylmethylphenol

Product 1

HCID 58266521HCID 58266521, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3,5-dichloro-4-piperidin-1-ylmethylphenol (290 mg, 1.1 mmol) and pyridine (0.36 mL, 4.5 mmol) in DCM (10 mL) at −20° C. was added trifluoromethanesulfonyl chloride (0.38 mL, 2.2 mmol). After the addition was complete the reaction was allowed to warm to ambient temperature and stirred for 10 minutes. The mixture was diluted with DCM (20 mL), washed with water (10 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in cyclohexane) to afford the title compound as a colourless oil (334 mg, 76%). 1H NMR (CDCl3, 300 MHz): 7.26 (s, 2H), 3.66 (s, 2H), 2.53-2.44 (m, 4H), 1.58-1.48 (m, 4H), 1.50-1.34 (m, 2H).

Workup

  1. additionAfter the addition
  2. washwashed with water (10 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by flash chromatography (silica, 12 g column, ISCO, 0-100% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-84ce44332bec4ade924b7ac9f5f333e1
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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