Triethylamine → HCID 19841179, compound

HRID 1638790Notes

Reaction equation

HRID 1638790 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:19](O)=[O:20])[CH2:15][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:22].Cl.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:36]=[C:37]([O:41][CH3:42])[C:38]=1[O:39][CH3:40])[CH2:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(N(CC)CC)C.P(C#N)(=O)(OCC)OCC>CN(C)C=O>[ClH:22].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:19]([N:33]3[CH2:34][CH2:35][N:30]([CH2:29][C:28]4[CH:27]=[C:26]([O:25][CH3:24])[C:38]([O:39][CH3:40])=[C:37]([O:41][CH3:42])[CH:36]=4)[CH2:31][CH2:32]3)=[O:20])[CH2:15][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochlorideHCID 146761973,4-Dihydro-6-(phenylmethoxy)-2-naphthalenecarboxylic acid

Product 1

HCID 19841179HCID 19841179, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 7-benzyloxy-1,2-dihydro-3-naphthoic acid (0.4 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (0.76 g), triethylamine (0.6 g), N,N-dimethylformamide (10 ml) and diethyl phosphorocyanidate (0.75 ml), an amidation as that described in Example 6 is carried out. The reaction 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-(7-benzyloxy-1,2-dihydro-3-naphthoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.6 g) as colorless crystals, m.p. 196°-199° C. (decomp.).

Workup

  1. customThe reaction 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

Sources & evidence

ORD record
ord-09768a9b76164aa7afc0ab5f07335e89
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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