Piperidine → HCID 18916388, compound

HRID 1290637Notes

Reaction equation

HRID 1290637 reaction equation
Cl[C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([Cl:14])[C:5]=2[N:6]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C(OCC)C>[N:15]1([C:2]2[S:3][C:4]3[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([Cl:14])[C:5]=3[N:6]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 12479783HCID 12479783, compound

Product 1

HCID 18916388HCID 18916388, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere a solution of 1.7 grams (6.8 mmole) of 2,4-dichloro-7-nitrobenzothiazole in 150 mL of diethyl ether was stirred as 1.2 grams (13.7 mmole) of piperidine was added via syringe over a ten minute period. The reaction mixture, which had spontaneously warmed, was cooled with ice-water to ambient temperature, where it stirred for 40 minutes. The resulting precipitate was collected by filtration and washed with 50 mL of ethyl acetate. The filtrate was washed with aqueous 0.1N hydrochloric acid and two 50 mL portions of water. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure, yielding a bright yellow-orange solid, which was combined with a material prepared by a similar route and purified by column chromatography on silica gel. Elution was accomplished with 7:1 followed by 5:1 hexane:ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure, yielding 1.3 grams of 2-(1-piperidinyl)-4-chloro-7-nitrobenzothiazole. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwas added via syringe over a ten minute period
  2. temperatureThe reaction mixture, which had spontaneously warmed
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with 50 mL of ethyl acetate
  5. washThe filtrate was washed with aqueous 0.1N hydrochloric acid and two 50 mL portions of water
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customyielding a bright yellow-orange solid, which
  10. customprepared by a similar route
  11. custompurified by column chromatography on silica gel
  12. washElution
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-56c6d7e25b24403bb7507b2c4598320f
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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