Hydrochloric Acid → HCID 20445319、化合物

HRID 2418713ノート

反応式

HRID 2418713 の反応式
C([O:5][C:6](=[O:8])[CH3:7])(C)(C)C.C([N-]C(C)C)(C)C.[Li+].[CH3:17][O:18][C:19]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][CH2:23][C:24]2=O.Cl.Cl.C(O)(=O)C>C1COCC1.O.CO>[CH3:17][O:18][C:19]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][CH:23]=[C:24]2[CH2:7][C:6]([OH:8])=[O:5]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 10908tert-Butyl acetateHCID 2724682Lithium diisopropylamideHCID 82192465,6-dimethoxy-1-tetraloneHCID 22641269Acetate-hydrochloric acid

生成物 1

HCID 20445319HCID 20445319、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

tert-Butylacetate is added to a solution of lithium di-isopropyl amide in THF at -78° C. To this solution is added 5,6-dimethoxy-1,2,3,4-tetrahydro-1-naphthalenone and the resulting mixture is stirred at 0° C. for 20 minutes, then cooled back to -78° C. One equivalent of HCl in water is added to the solution, followed by concentration of this mixture. The residue is heated with a solution of HCl/acetic acid (1:1) in water and methanol for 20 minutes, giving 5,6-dimethoxy-3,4-dihydronaphthalene-1-acetic acid. The latter acid is refluxed in benzene with PCl3 for one hour. This solution is filtered while hot, and the filtrate is concentrated and added to at 0° C. triethylamine and 1-(2-methoxyphenyl)piperazine in chloroform to give the corresponding amide. This intermediate product is reduced to the amine by refluxing in THF with lithium aluminum hydride for 2 hours and decomposing the excess lithium aluminum hydride with H2O and NaOH. The lithium and aluminum salts are removed, the THF concentrated, and the residue treated with HCl and isopropyl alcohol to yield 1-(2[4-(2-methoxyphenyl) piperazinyl]ethyl)-5,6-dimethoxy-3,4-dihydronaphthalene HCl.

後処理

  1. temperaturecooled back to -78° C

出典と根拠

ORDレコード
ord-7b8268082c5e4e70a95de794c6e54dbf
出典データセット
uspto-grants-1984_09
特許番号
US04473586

反応ノート

読み込み中…