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 1851823Notes

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. The operation for adding toluene to the obtained residue and distilling off it under reduced pressure was carried out 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
additionThe operation for adding toluene to the obtained residue
distillationdistilling off it under reduced pressure
customwas removed by azeotropic distillation

Sources & evidence

ORD record: ord-e4aa52b5772a4913874be8192cdfb576
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957205B2

Reaction notes

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