Triethylamine → HCID 19841239, compound

HRID 1638798Notes

Reaction equation

HRID 1638798 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[CH:7]=[C:8]([C:12]([OH:14])=O)[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]=1[O:17][CH3:18].[ClH:19].Cl.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(N(CC)CC)C.P(C#N)(=O)(OCC)OCC>CN(C)C=O>[ClH:19].[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[CH:7]=[C:8]([C:12]([N:30]3[CH2:29][CH2:28][N:27]([CH2:26][C:25]4[CH:33]=[C:34]([O:38][CH3:39])[C:35]([O:36][CH3:37])=[C:23]([O:22][CH3:21])[CH:24]=4)[CH2:32][CH2:31]3)=[O:14])[CH2:9][CH2:10][CH2:11][C:5]=2[C:4]=1[O:17][CH3:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 10467188HCID 10467188, compoundHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 19841239HCID 19841239, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a mixture of 3,4-dimethoxy6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (0.6 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1.3 g), triethylamine (1.5 g), N,N-dimethylformamide (20 ml) and diethyl phosphorocyanidate (0.6 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 ethyl acetate and ethyl ether to yield 1-(3,4-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.55 g) as colorless crystals, m.p. 225°-229° 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 ethyl acetate and ethyl ether

Sources & evidence

ORD record
ord-a674d7f71535476b86a46f0188a7fdcf
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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