Triethylamine → HCID 66692713, compound

HRID 710558Notes

Reaction equation

HRID 710558 reaction equation
NC1CCN(C(OC(C)(C)C)=O)CC1.[Cl:15]C(OC1C=CC=CC=1)=O.N1(CCC2C=CC([N:38]3[CH2:43][CH2:42][CH:41]([NH:44][C:45]([N:47]4[CH2:52][CH2:51][C:50](=[CH:53][C:54]5[CH:59]=[C:58]([F:60])[CH:57]=[CH:56][C:55]=5[F:61])[CH2:49][CH2:48]4)=[O:46])[CH2:40][CH2:39]3)=CC=2)C=CN=N1.CCN(CC)CC>C(#N)C.O>[ClH:15].[F:61][C:55]1[CH:56]=[CH:57][C:58]([F:60])=[CH:59][C:54]=1[CH:53]=[C:50]1[CH2:51][CH2:52][N:47]([C:45]([NH:44][CH:41]2[CH2:40][CH2:39][NH:38][CH2:43][CH2:42]2)=[O:46])[CH2:48][CH2:49]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 12682914-Amino-1-Boc-piperidineHCID 66692708HCID 66692708, compound

Product 1

HCID 66692713HCID 66692713, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

4-Amino-N-Boc-piperidine (5.00 g, 24.9 mmol) was dissolved in acetonitrile (100 mL), and phenyl chloroformate (3.46 mL, 27.4 mmol) was added dropwise thereto at 0° C., followed by stirring at room temperature for 3 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was dissolved in acetonitrile (50 mL), and the compound (2.88 g, 11.7 mmol) obtained in Example 34 (1) and Et3N (3.70 mL, 26.4 mmol) were added thereto, followed by stirring at 60° C. overnight. Water was added to the reaction mixture and the precipitate was collected by filtration, thereby giving tert-butyl 4-(4-(2,5-difluorobenzylidene)piperidine-1-carboxamido)piperidine-1-carboxylate (4.10 g, 38%) as a white solid. Following the procedure of Example 34 (1) and using this tert-butyl compound in place of tert-butyl 4-(2,5-difluorobenzylidene)piperidine-1-carboxylate, the title compound (quant.) was obtained as a white solid.

Workup

  1. customat 0° C.
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate
  5. filtrationAfter the desiccant was filtered off
  6. customthe residue obtained by evaporation under reduced pressure
  7. stirringby stirring at 60° C. overnight
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-7d9970b16b9945809c68852474fc85fa
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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