2,4-Dichloro-1,3,5-triazine → HCID 86685260, compound

HRID 522929Notes

Reaction equation

HRID 522929 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[Cl:29][C:30]1[N:35]=[C:34](Cl)[N:33]=[CH:32][N:31]=1>C(O)(C)C>[Cl:29][C:30]1[N:35]=[C:34]([N:13]2[CH2:14][CH2:15][CH:10]([O:9][CH2:8][C:7]3[CH:16]=[CH:17][C:4]([O:3][C:2]([F:18])([F:1])[F:19])=[CH:5][CH:6]=3)[CH2:11][CH2:12]2)[N:33]=[CH:32][N:31]=1

Participants

5

Reactant 3

HCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 18723226HCID 18723226, compound

Product 1

HCID 86685260HCID 86685260, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(4-(trifluoromethoxy)benzyloxy)piperidine (2.2 g, 8.00 mmol) in isopropanol (25 mL, 3 mL/mmol) was added DIPEA (3.6 mL, 0.02 mol) and 2,4-dichloro-1,3,5-triazine (1.2 g, 8.00 mmol) and the reaction was heated at 80° C. for 2 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 2-chloro-4-(4-((4-(trifluoromethoxy)benzyl)oxy)piperidin-1-yl)-1,3,5-triazine (800 mg, 57%) as a solid. Observed mass (M+1): 389.0.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-0b7f12f12a694c51a7603f3e905d2d4c
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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