Hydrochloric Acid → HCID 57421846, compound

HRID 2074276Notes

Reaction equation

[OH-].[Na+].C(O)(=O)C(O)=O.[F:9][C:10]1[CH:11]=[C:12]([CH:42]=[CH:43][CH:44]=1)[CH2:13][O:14][C:15]1[CH:41]=[CH:40][C:18]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]3[CH:30]=[N:31][CH:32]=[C:33]([CH2:35][O:36]C(=O)C)[CH:34]=3)=[O:27])[CH2:22][CH2:21]2)=[CH:17][CH:16]=1.Cl>C1COCC1>[F:9][C:10]1[CH:11]=[C:12]([CH:42]=[CH:43][CH:44]=1)[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][CH:29]3[CH2:34][CH:33]([CH2:35][OH:36])[CH2:32][NH:31][CH2:30]3)=[O:27])[CH2:22][CH2:21]2)=[CH:40][CH:41]=1

Participants

Conditions

Temperature: 65 °C

Procedure

An aqueous 1 M sodium hydroxide solution (7.65 ml) was added to a THF (20 ml) solution containing 5-[(acetoxy)methyl]pyridin-3-yl 4-{4-[(3-fluorobenzyl)oxy]phenoxy}piperidine-1-carboxylate oxalate (1.10 g), followed by stirring at 65° C. for 3 hours. The reaction liquid was neutralized with 1 M hydrochloric acid, followed by extraction with chloroform and drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=12:1 (v/v)) to obtain 5-(hydroxymethyl)piperidin-3-yl 4-{4-[(3-fluorobenzyl)oxy]phenoxy}piperidine-1-carboxylate (770 mg).

Workup

customThe reaction liquid
extractionfollowed by extraction with chloroform
dry with materialdrying over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=12:1 (v/v))

Sources & evidence

ORD record: ord-abac53f302f34de48eee73415ba95cc0
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919494B2

Reaction notes

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