Ethyl piperidine-2-carboxylate → N-(2,4-dichloro-6-fluorobenzothiazol-7-yl)-perhydroimidazo[1,5-a]pyridine-1,3-dione

HRID 21726

Reaction equation

HRID 21726 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([O:9]CC)=O.[Cl:12][C:13]1[S:14][C:15]2[C:21]([N:22]=[C:23]=[O:24])=[C:20]([F:25])[CH:19]=[C:18]([Cl:26])[C:16]=2[N:17]=1>O1CCCC1>[Cl:12][C:13]1[S:14][C:15]2[C:21]([N:22]3[C:7](=[O:9])[CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][N:1]4[C:23]3=[O:24])=[C:20]([F:25])[CH:19]=[C:18]([Cl:26])[C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 27517Ethyl piperidine-2-carboxylateHCID 111081572,4-Dichloro-6-fluoro-7-isocyanato-benzothiazole

Product 1

HCID 19933463N-(2,4-dichloro-6-fluorobenzothiazol-7-yl)-perhydroimidazo[1,5-a]pyridine-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.6 g Ethyl piperidine-2-carboxylate was added to a solution of 4.2 g 2,4-dichloro-6-fluoro-7-isocyanato-benzothiazole in 50 ml tetrahydrofuran. The mixture was heated for 5 hours under reflux. After cooling, the solvent was removed in vacuo and the residue recrystallised several times from ethyl acetate. Yield: 2.5 g=42% of theory m.p.: 168°-170° C.

Workup

  1. temperatureThe mixture was heated for 5 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customthe residue recrystallised several times from ethyl acetate

Sources & evidence

ORD record
ord-599d75b7d02443e5b36146fca1375b02
Source dataset
uspto-grants-1995_06
Patent number
US05424443

Linked notes

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