Hydrochloric Acid → 1-(7,8-Dimethoxy-1,2-dihydro-4-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

HRID 1638776Notes

Reaction equation

HRID 1638776 reaction equation
P(C#N)(=O)(OCC)OCC.[CH3:11][O:12][C:13]1[C:22]([O:23][CH3:24])=[C:21]2[C:16]([C:17]([C:25]([OH:27])=O)=[CH:18][CH2:19][CH2:20]2)=[CH:15][CH:14]=1.[ClH:28].Cl.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:42]=[C:43]([O:47][CH3:48])[C:44]=1[O:45][CH3:46])[CH2:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.Cl>C(OCC)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:28].[CH3:11][O:12][C:13]1[C:22]([O:23][CH3:24])=[C:21]2[C:16]([C:17]([C:25]([N:39]3[CH2:38][CH2:37][N:36]([CH2:35][C:34]4[CH:42]=[C:43]([O:47][CH3:48])[C:44]([O:45][CH3:46])=[C:32]([O:31][CH3:30])[CH:33]=4)[CH2:41][CH2:40]3)=[O:27])=[CH:18][CH2:19][CH2:20]2)=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochlorideHCID 198412007,8-Dimethoxy-1,2-dihydro-4-naphthoic acid

Product 1

HCID 198412141-(7,8-Dimethoxy-1,2-dihydro-4-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochlorideYield 67.7%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Diethyl phosphorocyanidate (1.2 ml) is added dropwise to a mixture of 7,8-dimethoxy-1,2-dihydro-4-naphthoic acid (0.5 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (0.87 g), triethylamine (0.86 g) and N,N-dimethylformamide (20 ml) with stirring. After stirring for one hour at room temperature, water (100 ml) is added to the reaction mixture and the mixture is extracted with ethyl acetate (100 ml). The organic layer is washed with water, dried and concentrated 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 ethyl ether and the solution is treated with 5N ethanolic hydrogen chloride (2 ml) to give 1-(7,8-dimethoxy-1,2-dihydro-4-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.75 g) as colorless powder.

Workup

  1. stirringAfter stirring for one hour at room temperature
  2. extractionthe mixture is extracted with ethyl acetate (100 ml)
  3. washThe organic layer is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily substance is purified by silica gel column chromatography (hexane: acetone=1:1)
  7. customThe product thus obtained

Sources & evidence

ORD record
ord-12d07bc7a4e142be87bcf8115211c9f3
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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