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

HRID 1726946Notes

Reaction equation

HRID 1726946 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-14dd62eab846404daa9dba48a8fc5493
Source dataset
uspto-grants-2009_02
Patent number
US07494998B2

Reaction notes

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