Triethylamine → 1-(6,7-Dibenzyloxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride

HRID 1638787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1638787
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][CH2:14][C:13]([C:27](O)=[O:28])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:30].Cl.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:44]=[C:45]([O:49][CH3:50])[C:46]=1[O:47][CH3:48])[CH2:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C(N(CC)CC)C.P(C#N)(=O)(OCC)OCC>CN(C)C=O>[ClH:30].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][CH2:14][C:13]([C:27]([N:41]1[CH2:40][CH2:39][N:38]([CH2:37][C:36]3[CH:44]=[C:45]([O:49][CH3:50])[C:46]([O:47][CH3:48])=[C:34]([O:33][CH3:32])[CH:35]=3)[CH2:43][CH2:42]1)=[O:28])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochlorideHCID 14676195HCID 14676195, Verbindung

Produkt 1

HCID 198411981-(6,7-Dibenzyloxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochlorideAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Using 6,7-dibenzyloxy-1,2-dihydro-3-naphthoic acid (0.5 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (0.69 g), triethylamine (0.52 g), N,N-dimethylformamide (10 ml) and diethyl phosphorocyanidate (0.75 ml), as amidation as that described in Example 6 is carried out. The product is purified by silica gel column chromatography (hexane:acetone=1:1-1:2) and converted to the hydrochloride in a mixture of ethyl acetate and ethyl ether to yield 1-(6,7-dibenzyloxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.6 g) as colorless crystals, m.p. 186°-190° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-21c9b13730c44f26af2463d54911811b
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04880809

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