HRID1662947

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1140

Toluene

C7H8

结构：OCCOCCN1CCN(C2=Nc3ccccc3Sc3ccccc32)CC1

HCID5002

Quetiapine

C21H25N3O2S

HCID444972

Fumaric acid

C4H4O4

PRODUCTS

生成物

结构：O=C(O)/C=C/C(=O)O.OCCOCCN1CCN(C2=Nc3ccccc3Sc3ccccc32)CC1.OCCOCCN1CCN(C2=Nc3ccccc3Sc3ccccc32)CC1

HCID5281025

Quetiapine fumarate

C46H54N6O8S2

收率 200%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: 20 °C

PROCEDURE

实验过程

A suspension of 1.62 g (0.014 mol) of fumaric acid in 100 ml of ethyl acetate is brought to the boil. At this temperature, 100 ml of a toluene solution containing 10.77 g (0.028 mol) of pure quetiapine base is added, and the reaction mixture is allowed to boil for about 5 minutes. During this period a crystalline product starts to precipitate, which is then cooled to ca. 20° C. and is stirred at this temperature for 60 minutes. After being sucked off and dried, approximately 12.28 g (0.028 mol) of quetiapine hemifumarate is obtained, i.e. 99% of the theory, having the HPLC purity 99.76%, and melting point 175.7° C.

WORKUP

后处理

additionis added
waitDuring this period a crystalline product starts
customto precipitate
customdried

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-849f65c8d38142a4a725e14d26031d9f
来源数据集: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08034805B2
来源说明: uspto-grants-2011_10

反应 SMILES

[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].C1(C)C=CC=CC=1.[CH:16]1[CH:17]=[CH:18][C:19]2[S:30][C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[C:22]([N:31]3[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])[CH2:33][CH2:32]3)[C:20]=2[CH:21]=1>C(OCC)(=O)C>[CH2:33]1[N:34]([CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])[CH2:35][CH2:36][N:31]([C:22]2[C:20]3[C:19](=[CH:18][CH:17]=[CH:16][CH:21]=3)[S:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH2:32]1.[CH2:33]1[N:34]([CH2:37][CH2:38][O:39][CH2:40][CH2:41][OH:42])[CH2:35][CH2:36][N:31]([C:22]2[C:20]3[C:19](=[CH:18][CH:17]=[CH:16][CH:21]=3)[S:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH2:32]1.[CH:2](/[C:1]([OH:8])=[O:7])=[CH:3]\[C:4]([OH:6])=[O:5]