Triethylamine → HCID 5181860, compound

HRID 1643467Notes

Reaction equation

HRID 1643467 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[CH2:21][OH:22].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([S:9]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[CH2:21][OH:22])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94263Piperidin-2-ylmethanolHCID 27332503-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 5181860HCID 5181860, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(Trifluoromethyl)benzenesulfonic acid chloride (1 eq), dissolved in methylene chloride (65 ml), was added dropwise to a cooled solution (0° C.) of 2-piperidinemethanol (40 mmol, 1.1 eq) in methylene chloride (160 ml) and triethylamine (2.5 eq). When the addition was complete, the cooling bath was removed and the reaction mixture was stirred at room temperature until, according to thin layer chromatography control, the reaction was complete (90 min). Hydrogen chloride solution (0.5 mol/l, 75 ml) was added, the mixture was stirred for 15 min, the phases were separated and the organic phase was washed with water, dried over sodium sulfate and concentrated in vacuo. Yield: 28%

Workup

  1. additionWhen the addition
  2. customthe cooling bath was removed
  3. custom(90 min)
  4. additionHydrogen chloride solution (0.5 mol/l, 75 ml) was added
  5. stirringthe mixture was stirred for 15 min
  6. customthe phases were separated
  7. washthe organic phase was washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b79cbd13708a4a4db28c4391c1e12819
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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