Benzoyl chloride, 3,4,5-trimethoxy- → [1,4-Bis(3,4,5-trimethoxybenzoyl)piperazin-2-yl]methyl diethylcarbamate

HRID 1860443Notes

Reaction equation

Cl.[CH2:2]([N:4]([C:7]([O:9][CH2:10][CH:11]1[CH2:16][NH:15][CH2:14][CH2:13][NH:12]1)=[O:8])[CH2:5][CH3:6])[CH3:3].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:22](Cl)=[O:23]>>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:22]([N:12]1[CH2:13][CH2:14][N:15]([C:22](=[O:23])[C:21]2[CH:20]=[C:19]([O:18][CH3:17])[C:27]([O:28][CH3:29])=[C:26]([O:30][CH3:31])[CH:25]=2)[CH2:16][CH:11]1[CH2:10][O:9][C:7]([N:4]([CH2:5][CH3:6])[CH2:2][CH3:3])=[O:8])=[O:23]

Participants

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-

HCID 70027687HCID 70027687, compound

Product 1

HCID 462383[1,4-Bis(3,4,5-trimethoxybenzoyl)piperazin-2-yl]methyl diethylcarbamateYield 80%

Procedure

Working again according to a protocol identical to the one used in step 1.3 of Example 1, followed by treating, under the same conditions as those of step 1.4 of Example 1, 0.5 g (1.73 mmol) of 2-(N,N-diethylaminocarbonyloxymethyl)piperazine hydrochloride with 1 g of 3,4,5-trimethoxybenzoyl chloride, 0.83 g of 1,4-bis(3′,4′,5′-trimethoxybenzoyl)-2-(N,N-diethylaminocarbonyloxymethyl)piperazine is obtained. Yield: 80%. Melting point: 128.6° C. Rf=0.35 (3/97 v/v MeOH/CH2Cl2).

Sources & evidence

ORD record: ord-fe135e91ad7440e69a9d941fbb4373f3
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531476B1

Reaction notes

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