Allylamine → HCID 178456915, compound

HRID 1620493Notes

Reaction equation

HRID 1620493 reaction equation
S=[C:2]1[CH2:6][S:5][C:4](=[O:7])[NH:3]1.[CH2:8]([NH2:11])[CH:9]=[CH2:10].S(C1C=CC(C)=CC=1)(O)(=O)=O.[F:23][C:24]([F:45])([F:44])[C:25]1[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:26]=1[CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([CH:34]=O)[CH2:30][CH2:29]1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>C(O)C>[F:23][C:24]([F:45])([F:44])[C:25]1[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:26]=1[CH2:27][N:28]1[CH2:33][CH2:32][CH:31](/[CH:34]=[C:6]2/[C:2]([NH:11][CH2:8][CH:9]=[CH2:10])=[N:3][C:4](=[O:7])[S:5]/2)[CH2:30][CH2:29]1

Participants

7

Reactant 5

HCID 7853AllylamineHCID 25517Ammonium ChlorideHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 23665647Potassium tert-butoxideHCID 866786841-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde tosylate

Product 1

HCID 178456915HCID 178456915, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-thioxo-1,3-thiazolidin-2-one (60 mg) in ethanol (2 mL) was added prop-2-en-1-amine (26 mg) at room temperature. The reaction mixture was stirred at room temperature for 2 hr. 1-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde tosylate (230 mg) and potassium tert-butoxide (101 mg) were added to the reaction mixture at room temperature, and the mixture was stirred at 80° C. for 3 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (95 mg).

Workup

  1. stirringthe mixture was stirred at 80° C. for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  7. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-5a519cf2e9ee42e0af5572da4f41a196
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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