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 448750Notes

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-79f6c66a0b814ba6bb3520cfacc8d2d6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481725B2

Reaction notes

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