Water → HCID 11493178, compound

HRID 2358064Notes

Reaction equation

HRID 2358064 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[C:10]([F:16])=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4]1)[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>C(Cl)Cl>[CH3:24][S:25]([O:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH:6]2[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]2)[C:10]=1[F:16])(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57438793HCID 57438793, compound

Product 1

HCID 11493178HCID 11493178, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(1-ethylpiperidin-4-yl)-2-fluorophenol (0.44 g, 1.97 mmol)) in methylene chloride (20 ml) was added triethylamine (4 ml) and methanesulfonyl chloride (0.56 ml, 3.67 mmol). The mixture was stirred for 20 h and water (50 ml) and methylene chloride (50 ml) was added and the phases were separated. The aqueous phase was extracted with methylene chloride (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated under reduced pressure to give an oil. Purification by flash column chromatography (ethyl acetate/methanol, 1:1) gave the title compound: 0.39 g (66%). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether: M.p. 161.5-163.2. MS m/z (relative intensity, 70 eV) 301 (M+, 15), 287 (15), 286 (bp), 222 (23), 207 (38).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with methylene chloride (2×50 ml)
  3. dry with materialthe combined organic phases was dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give an oil
  6. customPurification by flash column chromatography (ethyl acetate/methanol, 1:1)

Sources & evidence

ORD record
ord-5e1bd331744b427eba800cd4dd76dd6c
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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