Piperazine → 3-(Piperazin-1-yl)-1,2-benzoxazole

HRID 415132Notes

Reaction equation

HRID 415132 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>N1C=CC=CC=1>[N:11]1([C:2]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[O:4][N:3]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 27797803-Chloro-1,2-benzoxazole

Product 1

HCID 132324753-(Piperazin-1-yl)-1,2-benzoxazoleYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Chloro-1,2-benzisoxazole reacted with excess piperazine in the presence of pyridine to provide 3-(piperazin-1-yl)benzo[d]isoxazole (3A) in 76% yield. Reductive amination of compound (3A) with 2-carbomethoxy 2-methyl propionaldehyde gave alkylated piperazine (4A), which was purified over silica gel. Basic hydrolysis of the methyl ester of (4A) in aqueous ethanol followed by acidification gave the carboxylic acid (1) as the mono-HCl salt.

Sources & evidence

ORD record
ord-cae11d1a78c943df9591b7e68e4c0f79
Source dataset
uspto-grants-2012_01
Patent number
US08088778B2

Reaction notes

Loading…