Hydrochloric Acid → HCID 70873760, compound

HRID 2172188Notes

Reaction equation

Cl.O1CCCCC1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][C:22]3[O:23][C:24]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:25]=4[CH:26]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>C(O)C>[F:34][C:31]([F:32])([F:33])[C:28]1[CH:29]=[CH:30][C:24]2[O:23][C:22]([CH2:21][CH:18]3[CH2:19][CH2:20][N:15]([C:12]4[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=4)[CH2:16][CH2:17]3)=[CH:26][C:25]=2[CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1 N hydrochloric acid was added to an ethanol solution of 1-[4-(tetrahydropyran-2-yloxy)phenyl]-4-(5-trifluoromethylbenzofuran-2-ylmethyl)piperidine (2.3 g) and stirred at 80° C. for 1 hour. After being cooled to room temperature, a saturated sodium hydrogen carbonate aqueous solution was added to the mixture and concentrated under reduced pressure. The residue was subjected to extraction with ethyl acetate. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to afford the title compound as a pinkish white amorphous compound (1.15 g).

Workup

temperatureAfter being cooled to room temperature
concentrationconcentrated under reduced pressure
extractionThe residue was subjected to extraction with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-1f990fe3fdd14edc851a8242067bcc56
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051333B2

Reaction notes

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