HRID1374991

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID4875

Potassium iodide

HCID11430

Potassium Carbonate

CK2O3

结构：COCCOCOc1cc(CC2CNCCN2C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)ccc1C

HCID17963931

未命名化合物

HCID69419420

未命名化合物

PRODUCTS

生成物

结构：COCCOCOc1cc(CC2CN(CC#Cc3cccnc3)CCN2C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)ccc1C

HCID21076982

未命名化合物

收率 90.5%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A mixture of 1-[3,5-bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]piperazine (0.4 g), 1-chloro-3-(3-pyridyl)-2-propyne hydrochloride (0.17 g), potassium carbonate (0.52 g) and a trace of potassium iodide in N,N-dimethylformamide (7 ml) was stirred for 4 hours at 80° C. After cooling, the solvent was removed by evaporation, and ethyl acetate and aqueous sodium hydrogen carbonate solution were added thereto. The organic layer was separated, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate. The fractions containing the objective compound were collected and evaporated under reduced pressure to give 1-[3,5-bis(trifluoromethyl)benzoyl]-2-[3-[(2-methoxyethoxy)methoxy]-4-methylbenzyl]-4-[3-(3-pyridyl)-2-propynyl]piperazine (0.44 g) as an oil.

WORKUP

后处理

temperatureAfter cooling
customthe solvent was removed by evaporation, and ethyl acetate and aqueous sodium hydrogen carbonate solution
additionwere added
customThe organic layer was separated
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel
additionThe fractions containing the objective compound
customwere collected
customevaporated under reduced pressure

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a343710e88bd47988fb4ca32ca0842a1
来源数据集: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07166598B2
来源说明: uspto-grants-2007_01

反应 SMILES

[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[CH:16]=1)=[O:7].Cl.Cl[CH2:40][C:41]#[C:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[F:37][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:40][C:41]#[C:42][C:43]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)[CH2:10][CH:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28])[CH:16]=1)=[O:7]