Triethylamine → HCID 19841220, compound

HRID 1638799Notes

Reaction equation

HRID 1638799 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=O)=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[ClH:15].Cl.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)CC)C.P(C#N)(=O)(OCC)OCC>CN(C)C=O>[ClH:15].[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([N:26]3[CH2:25][CH2:24][N:23]([CH2:22][C:21]4[CH:29]=[C:30]([O:34][CH3:35])[C:31]([O:32][CH3:33])=[C:19]([O:18][CH3:17])[CH:20]=4)[CH2:28][CH2:27]3)=[O:14])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 28184935-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acidHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 19841220HCID 19841220, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 1-oxo-1,2,3,4-tetrahydro-6-naphthoic acid [Itoh et al., Chem. Pharm. Bull., 32, 130 (1984)] (0.8 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (2.25 g), triethylamine (1.7 g), N,N-dimethylformamide (10 ml) and diethyl phosphorocyanidate (1.6 ml), an amidation as that described in Example 6 is carried out. The product is purified by silica gel column chromatography (hexane:acetone=1:1), and converted to the hydrochloride in a mixture of ethanol, ethyl acetate and ethyl ether to give 1-(1-oxo-1,2,3,4-tetrahydro-6-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (1.5 g) as colorless crystals, m.p. 210°-215° C. (decomp.).

Workup

  1. customThe product is purified by silica gel column chromatography (hexane:acetone=1:1)
  2. additionconverted to the hydrochloride in a mixture of ethanol, ethyl acetate and ethyl ether

Sources & evidence

ORD record
ord-7e827cad3f5e4592b122c8f4b33de730
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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