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

HRID 1638775Notes

Reaction equation

HRID 1638775 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-16d30c72113b454391f2ad9cfccd6509
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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