Piperidine → HCID 57796650, compound

HRID 409701Notes

Reaction equation

HRID 409701 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:13][C:11]=2[N:12]=1>C(Cl)(Cl)Cl.CN(C=O)C>[CH3:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([S:17]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)(=[O:19])=[O:18])[CH:14]=[CH:13][C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 545939422-Methyl-1,3-benzoxazole-6-sulfonyl chloride

Product 1

HCID 57796650HCID 57796650, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Piperidine (2.2 g, 26 mmol) was added drop wise to a solution of Compound 8 (3.0 g, 10 mmol) in chloroform (30 ml) and DMF (10 ml). The combined mixture was stirred at room temperature for 1 hour, and then washed with water (2×, 50 ml) and brine (1×, 50 ml). The organic layer was then dried over sodium sulfate and evaporated to provide 2.76 g (76%) of Compound 9 as a sticky white solid. TLC analysis showed Rf=0.25 (30% ethyl acetate in hexane). The structure of this compound is given below:

Workup

  1. washwashed with water (2×, 50 ml) and brine (1×, 50 ml)
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-61327de12a0f4a38aeb0e06a97ef616f
Source dataset
uspto-grants-2014_06
Patent number
US08759526B2

Reaction notes

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