1-[[[4-(4-Propylpiperazin-1-yl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid hydrochloride → 2-[4-(4-Propylpiperazin-1-yl)phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one hydrochloride

HRID 73844Notes

Reaction equation

[ClH:1].[CH2:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH:19][C:20]3([C:26]([OH:28])=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)[CH2:3][CH3:4]>C(OC(=O)C)(=O)C>[ClH:1].[CH2:2]([N:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:28][C:26](=[O:27])[C:20]4([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]4)[N:19]=3)=[CH:13][CH:12]=2)[CH2:9][CH2:10]1)[CH2:3][CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

After a suspension of 631 mg (1.54 mmol) of 1-[[[4-(4-propylpiperazin-1-yl)phenyl]carbonyl]amino]cyclohexanecarboxylic acid hydrochloride in 18 ml of acetic anhydride was stirred at 100° C. for 1 hour, the reaction solution was concentrated under reduced pressure. Toluene was added to the obtained residue, it was distilled off under reduced pressure three times, and acetic anhydride was removed by azeotropic distillation to obtain 500 mg (83%) of the title compound.

Workup

concentrationthe reaction solution was concentrated under reduced pressure
additionToluene was added to the obtained residue, it
distillationwas distilled off under reduced pressure three times, and acetic anhydride
customwas removed by azeotropic distillation

Sources & evidence

ORD record: ord-12b502c590f642ac9c7cef359ce9cca9
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829209B2

Reaction notes

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