三乙胺 → 1-(Benzo[1,2,3]thiadiazole-5-carbonyl)-piperidin-4-one

HRID 349753

反应方程式

HRID 349753 反应方程式
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

参与物

7

反应物 4

HCID 8471三乙胺HCID 68263N,N'-羰基二咪唑HCID 2735458苯并-1,2,3-噻二唑-5-羧酸HCID 30848514-Piperidone hydrochloride

产物 1

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

试剂、催化剂与溶剂 2

HCID 8028四氢呋喃溶剂HCID 8857乙酸乙酯溶剂

实验过程

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).

后处理

  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)

来源与证据

ORD记录
ord-c814a59f7360487483b868588ecd4942
来源数据集
uspto-grants-2007_02
专利号
US07179922B2

关联笔记

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