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

HRID 1913158

Reaktionsgleichung

Reaktionsgleichung von HRID 1913158
[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

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 670728Methyl 1-(biphenyl-4-ylcarbonyl)piperidine-4-carboxylate

Produkt 1

HCID 8930531-([1,1'-Biphenyl]-4-carbonyl)piperidine-4-carboxylic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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].

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-cd9c43cb862f460e8bf104934bd03c73
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609696B2

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