Piperidin-4-ol → HCID 67322152, compound

HRID 1846636Notes

Reaction equation

Br[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[NH:17][C:18](=[O:26])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH2:6][CH2:5]1.[OH:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[C:18]([NH:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[N:7]1[CH2:8][CH2:9][CH:4]([CH2:3][CH2:2][N:31]2[CH2:32][CH2:33][CH:28]([OH:27])[CH2:29][CH2:30]2)[CH2:5][CH2:6]1)=[O:26]

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of 0.040 g (0.088 mmol) of N-{2-[4-(2-bromo-ethyl)-piperidin-1-yl]-5-chloro-phenyl}-3-chloro-benzamide, 0.044 g (0.44 mmol) of 4-hydoxypiperidine, and 0.50 mL (2.9 mmol) of N,N-diisopropylethylamine in acetonitrile (1 mL) is heated to 175° C. in a microwave reactor for 30 minutes. The mixture is cooled to room temperature and purified by preparative reverse phase HPLC to provide 0.023 g (55%) of the title compound (100) as a colorless solid. [M+H]+=476.3.

Workup

temperatureThe mixture is cooled to room temperature
custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-c1a3f4f76aad462a9256a7a2df68eecb
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952004B2

Reaction notes

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