Hydrochloric Acid → 1-([1,1'-Biphenyl]-4-carbonyl)piperidine-4-carboxylic acid

HRID 1913158

Reaction equation

[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17]C)=[O:16])[CH2:11][CH2:10]2)=[O:8])=[CH:3][CH:2]=1.[OH-].[Na+].O.Cl>O1CCCC1>[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:2]=[CH:3][C:4]([C:7]([N:9]2[CH2:10][CH2:11][CH:12]([C:15]([OH:17])=[O:16])[CH2:13][CH2:14]2)=[O:8])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A stirred mixture of methyl 1-(biphenyl-4-ylcarbonyl)piperidine-4-carboxylate (0.10 g, 0.31 mmol), sodium hydroxide (25 mg, 0.62 mmol), water (4 mL) and tetrahydrofuran (1 mL) is heated at 50° C. for 3 h. Solvents are removed under reduced pressure giving a residue. The residue is redissolved 1M aqueous HCl (4 mL) and extracted with EtOAc (3×4 mL). The organic layers are combined, dried (Na2SO4), filtered and concentrated under reduced pressure to give 82 mg (93%) of 1-(biphenyl-4-ylcarbonyl)piperidine-4-carboxylic acid. m/z=310 [M++H].

Workup

customSolvents are removed under reduced pressure
customgiving a residue
extractionextracted with EtOAc (3×4 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cd9c43cb862f460e8bf104934bd03c73
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609696B2

Linked notes

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