Ethylparaben → 1-[4-(4-Fluorobenzyloxy)benzoyl]-4-isobutylpiperazine

HRID 1292103Notes

Reaction equation

HRID 1292103 reaction equation
OC1C=CC(C(OCC)=O)=CC=1.FC1C=CC(CBr)=CC=1.[F:22][C:23]1[CH:39]=[CH:38][C:26]([CH2:27][O:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([OH:35])=O)=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.[CH2:40]([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)[CH:41]([CH3:43])[CH3:42]>>[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([N:47]3[CH2:48][CH2:49][N:44]([CH2:40][CH:41]([CH3:43])[CH3:42])[CH2:45][CH2:46]3)=[O:35])=[CH:36][CH:37]=2)=[CH:38][CH:39]=1

Participants

5

Reactant 4

HCID 8434EthylparabenHCID 680214-Fluorobenzyl bromideHCID 9615954-(4-Fluoro-benzyloxy)-benzoic acidHCID 20520521-(2-Methylpropyl)piperazine

Product 1

HCID 189142221-[4-(4-Fluorobenzyloxy)benzoyl]-4-isobutylpiperazineYield 58.4%

Procedure

It was synthesized in the manner identical to Example 3. Namely, ethyl 4-hydroxybenzoate (2.50 g) was benzylated with 4-fluorobenzyl bromide (2.84 g) and then hydrolyzed. From thus obtained 3.57 g of 4-(4-fluorobenzyloxy) benzoic acid, 1.24 g was subjected to a condensation reaction with 1-isobutylpiperazine (0.71 g), thereby yielding 1.08 g of the aimed compound.

Workup

  1. customIt was synthesized in the manner identical to Example 3

Sources & evidence

ORD record
ord-4e9d99ad29fd4b6582547c489d922c2d
Source dataset
uspto-grants-1998_05
Patent number
US05756505

Reaction notes

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