HRID1579329

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID4875

Potassium iodide

HCID516893

Potassium bicarbonate

CHKO3

HCID2723694

4'-Tert-butyl-4-chlorobutyrophenone

C14H19ClO

HCID21568361

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(C(=C2CCN(CCCC(=O)c3ccc(C(C)(C)C)cc3)CC2)c2ccccc2)cc1.Cl

HCID21568347

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID1140

Toluene

C7H8

2 次

PROCEDURE

实验过程

A mixture of 25.4 g (0.0905 mole) of α-phenyl-α-(p-tolyl)-4-piperidinemethanol, 26.2 g (0.11 mole) of 4'-tert-butyl-4-chlorobutyrophenone, 22 g of potassium bicarbonate, 0.1 g of potassium iodide, 250 ml of toluene, and 40 ml of water is refluxed for 88 hours. Upon cooling to room temperature the toluene layer is separated, and the aqueous layer is extracted with toluene. The combined toluene extracts are dried over magnesium sulfate, filtered and the filtrate is treated with ethereal HCl. The resulting precipitate is filtered, triturated with ether, and recrystallized from butanone-ether to give 4'-tert-butyl-4-[4-[α-(p-tolyl)benzylidene]piperidino]butyrophenone hydrochloride, M.P. 187°-189°C.

WORKUP

后处理

temperatureis refluxed for 88 hours
customis separated
extractionthe aqueous layer is extracted with toluene
dry with materialThe combined toluene extracts are dried over magnesium sulfate
filtrationfiltered
additionthe filtrate is treated with ethereal HCl
filtrationThe resulting precipitate is filtered
customtriturated with ether
customrecrystallized from butanone-ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1d273f2d1eb44a9b86ee18af9ea6bf92
来源数据集: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US03931197
来源说明: uspto-grants-1976_01

反应 SMILES

[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:37])[CH2:33][CH2:34][CH2:35][Cl:36])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].C(=O)(O)[O-].[K+].[I-].[K+]>C1(C)C=CC=CC=1.O>[ClH:36].[C:22]([C:26]1[CH:27]=[CH:28][C:29]([C:32](=[O:37])[CH2:33][CH2:34][CH2:35][N:12]2[CH2:13][CH2:14][C:9](=[C:7]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:10][CH2:11]2)=[CH:30][CH:31]=1)([CH3:25])([CH3:24])[CH3:23]