Hydrochloric Acid → 1-(6,7-Dimethoxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

HRID 1638779Notes

Reaction equation

HRID 1638779 reaction equation
P(C#N)(=O)(OCC)OCC.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[CH2:19][CH2:18][C:17]([C:25]([OH:27])=O)=[CH:16]2.[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)(=O)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:28].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[CH2:19][CH2:18][C:17]([C:25]([N:39]1[CH2:38][CH2:37][N:36]([CH2:35][C:34]3[CH:42]=[C:43]([O:47][CH3:48])[C:44]([O:45][CH3:46])=[C:32]([O:31][CH3:30])[CH:33]=3)[CH2:41][CH2:40]1)=[O:27])=[CH:16]2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochlorideHCID 14676173HCID 14676173, compound

Product 1

HCID 198412181-(6,7-Dimethoxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl phosphorocyanidate (1 ml) is added dropwise, under ice-cooling, to a mixture of 1,2-dihydro-6,7-dimethoxy-3-naphthoic acid (0.8 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1 g), triethylamine (0.35 g) and N,N-dimethylformamide (30 ml). The whole mixture is stirred for one hour under ice-cooling and allowed to stand at room temperature for one hour. 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 residue is purified silica gel column chromatography (hexane:acetone=1:1-1:2). The oily product thus obtained is treated with hydrogen chloride is ethyl acetate to afford 1-(6,7-dimethoxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride, which is identical with the product obtained in Example 5. The yield is 0.85 g.

Workup

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

Sources & evidence

ORD record
ord-22ebf7425221482d83e436792b7e5de8
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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