Acetic Anhydride → 1-(6,7-Diacetyloxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine fumarate

HRID 1638793Notes

Reaction equation

HRID 1638793 reaction equation
Br.[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[CH2:9][CH2:8][C:7]([C:14]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)[CH2:18][CH2:17]1)=[O:15])=[CH:6]2.[C:35](OCC)(=[O:37])[CH3:36].[C:41](OC(=O)C)(=[O:43])[CH3:42].[C:48]([OH:55])(=[O:54])/[CH:49]=[CH:50]/[C:51]([OH:53])=[O:52]>C(OCC)C.C(O)C.C(N(CC)CC)C>[C:48]([OH:55])(=[O:54])/[CH:49]=[CH:50]/[C:51]([OH:53])=[O:52].[C:35]([O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:41](=[O:43])[CH3:42])[CH2:9][CH2:8][C:7]([C:14]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:24]=[C:25]([O:33][CH3:34])[C:26]([O:31][CH3:32])=[C:27]([O:29][CH3:30])[CH:28]=3)[CH2:18][CH2:17]1)=[O:15])=[CH:6]2)(=[O:37])[CH3:36]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 444972Fumaric AcidHCID 198412291-(6,7-Dihydroxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrobromide

Product 1

HCID 198411821-(6,7-Diacetyloxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine fumarate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(6,7-dihydroxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrobromide (0.3 g), ethyl acetate (20 ml), triethylamine (0.5 ml) and acetic anhydride (0.5 ml) is left standing at room temperature overnight. Ethanol (5 ml) is added to the mixture. The whole mixture is left standing for one hour and then concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane:acetone=1:1-1:2) to give an oily product. This product is dissolved in ethyl ether. An ethyl ether solution (50 ml) of fumaric acid (0.1 g) is added to the solution. The mixture is diluted with petroleum ether, whereupon colorless powder precipitates out. The precipitates are collected by filtration to give 1-(6,7-diacetyloxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine fumarate (0.25 g) as colorless powder.

Workup

  1. waitis left
  2. waitThe whole mixture is left
  3. waitstanding for one hour
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (hexane:acetone=1:1-1:2)
  6. customto give an oily product
  7. customprecipitates out
  8. filtrationThe precipitates are collected by filtration

Sources & evidence

ORD record
ord-9691fe14975841d0909ca6d5237e365f
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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