Triethylamine → HCID 66691794, compound

HRID 710557Notes

Reaction equation

HRID 710557 reaction equation
ClC(OC1C=CC=CC=1)=O.[F:11][C:12]([F:22])([F:21])[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16][CH2:15]1.N1(CCC2C=CC(N3CCC(N[C:43]([N:45]4[CH2:50][CH2:49][C:48](=[CH:51][C:52]5[CH:57]=[C:56]([F:58])[CH:55]=[CH:54][C:53]=5[F:59])[CH2:47][CH2:46]4)=[O:44])CC3)=CC=2)C=CN=N1.CCN(CC)CC>C(#N)C.CC(N(C)C)=O.O>[F:59][C:53]1[CH:54]=[CH:55][C:56]([F:58])=[CH:57][C:52]=1[CH:51]=[C:48]1[CH2:49][CH2:50][N:45]([C:43]([NH:20][CH:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:12]([F:11])([F:21])[F:22])[CH2:15][CH2:16]2)=[O:44])[CH2:46][CH2:47]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 162287221-(2,2,2-Trifluoroethyl)piperidin-4-amineHCID 66692708HCID 66692708, compound

Product 1

HCID 66691794HCID 66691794, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

Phenyl chloroformate (200 μL, 1.57 mmol) was added dropwise to 1-(2,2,2-trifluoroethyl)piperidin-4-amine (400 mg, 1.57 mmol) dissolved in a mixed solvent of acetonitrile (3 mL) and dimethylacetamide (1 mL) at 0° C., followed by stirring at the same temperature for 1 hour, and 4-(2,5-difluorobenzylidene)piperidine hydrochloride (580 mg, 2.36 mmol) obtained in Example 34 (1) and Et3N (430 μL) were added thereto, followed by stirring at 60° C. overnight. Water was added to the reaction mixture, and after extraction with chloroform, the extract was washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:50), thereby giving the title compound (110 mg, 17%) as a white solid.

Workup

  1. stirringby stirring at 60° C. overnight
  2. extractionafter extraction with chloroform
  3. washthe extract was washed with water
  4. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. customthe residue obtained by evaporation under reduced pressure
  7. customwas purified

Sources & evidence

ORD record
ord-26b8ceacb1de41eda3b772717718391f
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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