HRID1598591

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID222

Ammonia gas

H3N

HCID1118

Sulfuric acid

H2O4S

结构：CO[C@@H]1CN(CCCC2(C)OCCO2)CC[C@@H]1NC(=O)c1cc(Cl)c(N)c2c1OC(C)(C)C2

HCID67712855

未命名化合物

PRODUCTS

生成物

结构：CO[C@@H]1CN(CCCC(C)=O)CC[C@@H]1NC(=O)c1cc(Cl)c(N)c2c1OC(C)(C)C2.CO[C@@H]1CN(CCCC(C)=O)CC[C@@H]1NC(=O)c1cc(Cl)c(N)c2c1OC(C)(C)C2.O

HCID131718804

未命名化合物

收率 51.6%

PROCEDURE

实验过程

A mixture of 5.4 parts of cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-[3-(2-methyl-1,3-dioxolan-2-yl)propyl]-4-piperidinyl]-2,2-dimethyl-7-benzofurancarboxamide and 85 ml of an aqueous sulfuric acid solution 1% was stirred for 2 hours at reflux temperature. After cooling, the reaction mixture was basified with ammonia and extracted with dichloromethane (2x). The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was suspended in 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.4 parts (51.6%) of cis-4-amino-5-chloro-2,3-dihydro-N-[3-methoxy-1-(4-oxopentyl)-4-piperidinyl]-2,2-dimethyl-7-benzofurancarboxamide hemihydrate; mp. 137.7° C. (comp. 112).

WORKUP

后处理

temperatureat reflux temperature
temperatureAfter cooling
extractionextracted with dichloromethane (2x)
customThe combined extracts were dried
filtrationfiltered
customevaporated
customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5)
customThe eluent of the desired fraction was evaporated
filtrationThe product was filtered off
customdried

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-5c21092dea684e48a5db4baa9db84116
来源数据集: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05739134
来源说明: uspto-grants-1998_04

反应 SMILES

[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]3([CH3:30])OCC[O:26]3)[CH2:18][C@H:17]2[O:31][CH3:32])=[O:14])=[CH:4][C:3]=1[Cl:33].S(=O)(=O)(O)O.N>>[OH2:10].[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:11])([CH3:12])[O:10][C:6]=2[C:5]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25](=[O:26])[CH3:30])[CH2:18][C@H:17]2[O:31][CH3:32])=[O:14])=[CH:4][C:3]=1[Cl:33].[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:11])([CH3:12])[O:10][C:6]=2[C:5]([C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25](=[O:26])[CH3:30])[CH2:18][C@H:17]2[O:31][CH3:32])=[O:14])=[CH:4][C:3]=1[Cl:33]