HRID584207

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID712

Formaldehyde

CH2O

HCID81531

Diisopropylethylamine

C8H19N

HCID22342863

3,3-Dimethylmorpholine--hydrogen chloride (1/1)

C6H14ClNO

结构：C#CCN1CCN(C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)[C@H](Cc2ccc(C)c(C)c2)C1

HCID53973560

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(C[C@@H]2CN(CC#CCN3CCOCC3(C)C)CCN2C(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc1C

HCID54544444

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID24350

Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)

CuI

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 70 °C

PROCEDURE

实验过程

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(2-propynyl)piperazine (0.49 g), 3,3-dimethylmorpholine hydrochloride (0.185 g), paraformaldehyde (62 mg), diisopropylethylamine (0.21 ml), and copper (1) iodide (20 mg) in 1,4-dioxane (5 ml) was stirred at 70° C. for 1.5 hours. After removal of the solvent by evaporation, the residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (40:1). The fractions containing the objective compound was collected and evaporated under reduced pressure to give a syrup of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-(3,3-dimethylmorpholino)-2-butynyl]piperazine (0.45 g).

WORKUP

后处理

customAfter removal of the solvent
customby evaporation
customthe residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (40:1)
additionThe fractions containing the objective compound
customwas collected
customevaporated under reduced pressure

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6e2168cc59894a8d9dd299507199d71b
来源数据集: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06924278B2
来源说明: uspto-grants-2005_08

反应 SMILES

[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[CH:16])[CH2:10][C@H:9]1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([CH3:25])[CH:19]=1)=[O:7].Cl.[CH3:36][C:37]1([CH3:43])[CH2:42][O:41][CH2:40][CH2:39][NH:38]1.C=O.[CH:46](N(C(C)C)CC)(C)C>O1CCOCC1.[Cu]I>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:46][N:38]2[CH2:39][CH2:40][O:41][CH2:42][C:37]2([CH3:43])[CH3:36])[CH2:10][C@H:9]1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([CH3:25])[CH:19]=1)=[O:7]