Triethylamine → 1-(Benzo[1,2,3]thiadiazole-5-carbonyl)-piperidin-4-one

HRID 1060819

Reaction equation

HRID 1060819 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([OH:24])=O)=[CH:21][C:16]=2[N:15]=[N:14]1.Cl.[NH:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([N:26]3[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]3)=[O:24])=[CH:21][C:16]=2[N:15]=[N:14]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27354581,2,3-Benzothiadiazole-5-carboxylic acidHCID 30848514-Piperidone hydrochloride

Product 1

HCID 223974651-(Benzo[1,2,3]thiadiazole-5-carbonyl)-piperidin-4-oneYield 29.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

CDI (4.5 g) added to a solution of the benzo[1,2,3]thiadiazole-5-carboxylic acid (5 g) stirring in THF (100 ml) at RT. After 1 hour 4-piperidone hydrochloride (3.7 g) and triethylamine (4.3 ml) were added and the mixture stirred overnight. The resulting mixture was diluted with ethyl acetate, washed with 2M HCl (100 ml), saturated NaHCO3 solution (200 ml) and then with saturated brine (200 ml). The organic layer was dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography (silica, eluting with mixtures of ethyl acetate in dichloromethane) to give the product as a yellow oil (2.1 g; MS: APCI+(M+H)262).

Workup

  1. washwashed with 2M HCl (100 ml), saturated NaHCO3 solution (200 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto leave a residue which
  5. customwas purified by column chromatography (silica, eluting with mixtures of ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-2aa1078eaa52461b9b5ae61e9cdc1257
Source dataset
uspto-grants-2003_02
Patent number
US06525070B2

Linked notes

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