1-Piperazinecarboxylic acid, ethyl ester → HCID 14350496, compound

HRID 1382712Notes

Reaction equation

HRID 1382712 reaction equation
[N:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:12][C:13]1[C:14](=[O:23])[C:15]2[C:16]([C:20](=[O:22])[CH:21]=1)=[N:17][S:18][N:19]=2>C(O)C>[Cl:12][C:13]1[C:14](=[O:23])[C:15]2=[N:19][S:18][N:17]=[C:16]2[C:20](=[O:22])[C:21]=1[N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 12573840HCID 12573840, compound

Product 1

HCID 14350496HCID 14350496, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 332 mg of 1-piperazinecarboxylic acid, ethyl ester and 200.6 mg of 5-chloro-2,1,3-benzothiadiazole-4,7-dione in absolute ethanol was heated at reflux, with stirring. The mixture was then stirred for 2 hours at room temperature, evaporated, chromatographed on silica gel, eluting with chloroform and concentrated to a red oil. This oil was crystallized from dichloromethanehexane, giving 50 mg of the desired product, mp 152°-154° C.

Workup

  1. temperatureat reflux
  2. stirringThe mixture was then stirred for 2 hours at room temperature
  3. customevaporated
  4. customchromatographed on silica gel
  5. washeluting with chloroform
  6. concentrationconcentrated to a red oil
  7. customThis oil was crystallized from dichloromethanehexane

Sources & evidence

ORD record
ord-b02136a9cc844f7686b59500c0583506
Source dataset
uspto-grants-1989_02
Patent number
US04808586

Reaction notes

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