Piperidine → HCID 67381605, compound

HRID 909357Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([CH2:16][CH2:17][CH2:18][O:19][CH:20]([CH3:22])[CH3:21])[C:14]([CH2:23][O:24][CH2:25][CH3:26])=[N:13][C:7]=3[CH:8]=[N+:9]([O-:12])[C:10]=2[CH:11]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>O>[CH2:25]([O:24][CH2:23][C:14]1[N:15]([CH2:16][CH2:17][CH2:18][O:19][CH:20]([CH3:22])[CH3:21])[C:6]2[C:5]3[CH:4]=[CH:3][C:2]([N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:11][C:10]=3[N+:9]([O-:12])=[CH:8][C:7]=2[N:13]=1)[CH3:26]

Participants

Conditions

Temperature: 150 °C

Procedure

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline-5-oxide (0.500 g), water (4.0 mL), and piperidine (1.0 mL) were added sequentially to a 20 mL steel pressure vessel. The vessel was sealed and then heated in an oven at 150° C. for 16 hours. The reaction mixture was allowed to cool and then was extracted with chloroform (×2). The combined extracts were washed sequentially with water and brine and then dried over sodium sulfate. This material was combined with that from another run on the same scale and then purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument using a silica gel cartridge and eluting with a gradient of 2-22% CMA in chloroform to provide 0.137 g of 2-ethoxymethyl-1-(3-isopropoxypropyl)-7-(piperidin-1-yl)-1H-imidazo[4,5-c]quinoline-5-oxide as a brown oil.

Workup

customThe vessel was sealed
temperatureto cool
extractionwas extracted with chloroform (×2)
washThe combined extracts were washed sequentially with water and brine
dry with materialdried over sodium sulfate
custompurified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument
washeluting with a gradient of 2-22% CMA in chloroform

Sources & evidence

ORD record: ord-c35d8d1a2a3a4af4905372214dec3137
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017779B2

Reaction notes

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