Hydrochloric Acid → 1-(7-Methoxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

HRID 1638775

反応式

HRID 1638775 の反応式
[ClH:1].Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[CH2:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N([CH2:27][CH3:28])CC)C.[OH2:29].Cl.O1[CH2:36][CH2:35][O:34][CH2:33]C1>C(O)C>[ClH:1].[CH3:33][O:34][C:35]1[CH:36]=[C:15]2[C:7]([CH:8]=[C:28]([C:27]([N:12]3[CH2:13][CH2:14][N:9]([CH2:8][C:7]4[CH:6]=[C:5]([O:4][CH3:3])[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=4)[CH2:10][CH2:11]3)=[O:29])[CH2:17][CH2:16]2)=[CH:6][CH:5]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 312751,4-Dioxane2 回HCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

生成物 1

HCID 198412211-(7-Methoxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 7-methoxy-1,2-dihydro-3-naphthoic acid [Jacques et al., Bull. Soc. Chim. Fr., 512 (1950)] (2 g), benzene (50 ml) and thionyl chloride (2 ml) is heated under reflux for one hour. After distilling off the solvent under reduced pressure, benzene (50 ml) is added and the benzene is distilled off again under reduced pressure. The 7-methoxy-1,2-dihydro-3-naphthoyl chloride thus obtained is dissolved in dioxane (10 ml). The solution is added dropwise to a mixture of 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (2.6 g), dioxane (50 ml) and triethylamine (5 ml) at room temperature with stirring. Then the mixture is stirred at room temperature for 30 minutes. Water (300 ml) is added to the mixture, which is extracted with ethyl acetate. The extract solution is washed with a dilute aqueous solution of sodium hydroxide and water, then the solvent is distilled off under reduced pressure. The resulting oily substance is purified by silica gel column chromatography (hexane:acetone=1:1). The product thus obtained is dissolved in ethanol and the solution is treated with on ethanolic hydrogen chloride (5 ml) to give 1-(7-methoxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (2.9 g) as colorless crystals, m.p. 210°-215° C. (decomp.).

後処理

  1. stirringThen the mixture is stirred at room temperature for 30 minutes
  2. extractionis extracted with ethyl acetate
  3. washThe extract solution is washed with a dilute aqueous solution of sodium hydroxide and water
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe resulting oily substance is purified by silica gel column chromatography (hexane:acetone=1:1)
  6. customThe product thus obtained

出典と根拠

ORDレコード
ord-16d30c72113b454391f2ad9cfccd6509
出典データセット
uspto-grants-1989_11
特許番号
US04880809

関連ノート

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