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

HRID 1638801Notes

Reaction equation

HRID 1638801 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]([OH:15])=O)[CH2:9][CH2:10]2)=[CH:5][CH:4]=1.[ClH:16].Cl.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[CH2:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.P(C#N)(=O)(OCC)OCC.Cl.[C:48]([O:51][CH2:52]C)(=O)C>CN(C)C=O.C(N(CC)CC)C>[ClH:16].[CH3:48][O:51][CH2:52][CH2:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]([N:27]3[CH2:28][CH2:29][N:24]([CH2:23][C:22]4[CH:21]=[C:20]([O:19][CH3:18])[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=4)[CH2:25][CH2:26]3)=[O:15])[CH2:9][CH2:10]2)=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 76257Diethyl cyanophosphonateHCID 127384776-Methoxy-3,4-dihydronaphthalene-2-carboxylic acidHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 198412191-(7-Methoxyethoxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Using 7-methoxy-1,2-dihydro-3-naphthoic acid (0.5 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1.1 g), triethylamine (0.81 g), N,N-dimethylformamide (20 ml) and diethyl phosphorocyanidate (1 ml), an amidation is carried out in a manner as that described in Example 6. The reaction product is purified by silica gel column chromatography (hexane:acetone=1:1-1:2) to afford an oily product, which is converted to the hydrochloride in ethyl acetate to give 1-(7-methoxyethoxy-1,2-dihydro-3-naphthoyl)- 4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.8 g) as colorless crystals, m.p. 187°-190° C.

Workup

  1. customThe reaction product is purified by silica gel column chromatography (hexane:acetone=1:1-1:2)
  2. customto afford an oily product, which

Sources & evidence

ORD record
ord-9765219775e04643b72965b1047bdef1
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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