Triethylamine → 6-Chlorobenzo[d]isoxazol-3-yl 4-methylpiperidine-1-carboxylate

HRID 1409986Notes

Reaction equation

HRID 1409986 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([OH:9])=[N:7][O:8][C:4]=2[CH:3]=1.[CH3:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19](Cl)=[O:20])[CH2:15][CH2:14]1.C(N(CC)CC)C>N1C=CC=CC=1>[CH3:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:9][C:6]2[C:5]3[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=3[O:8][N:7]=2)=[O:20])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152215164-Methylpiperidine-1-carbonyl ChlorideHCID 178518989HCID 178518989, compound

Product 1

HCID 120014166-Chlorobenzo[d]isoxazol-3-yl 4-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

200 mg (1.18 mmol) of 6-chlorobenzo[d]isoxazol-3-ol, 228.7 mg (1.41 mmol) of 4-methylpiperidine-1-carbonyl chloride and 164 μl (2.36 mmol) of triethylamine were dissolved in 10 ml of pyridine and stirred at room temperature for 24 h. The reaction mixture was concentrated, and the residue was dissolved in water and extracted with ethyl acetate. The organic phase was concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 147 mg (42%), M+H+: 295.2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase was concentrated
  5. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-3010e090d5c64ce6b53f16ac35506f09
Source dataset
uspto-grants-2014_12
Patent number
US08921404B2

Reaction notes

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