Hydrochloric Acid → HCID 69008872, Verbindung

HRID 1773465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773465
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Li+].Cl>CO.C1COCC1.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([NH:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=3)=[O:16])[CH2:12][CH2:13]2)=[CH:27][CH:28]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57951063HCID 57951063, Verbindung

Produkt 1

HCID 69008872HCID 69008872, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

Methyl 4-(1-(4-cyanobenzyl)piperidin-4-ylcarbamoyl)benzoate (900 mg, 2.38 mmol) and lithium hydroxide (600 mg, 14.28 mmol) was added to MeOH/THF/H2O (2/1/1, 20 mL), and the mixture was stirred overnight, then acidified with 2M hydrochloric acid (10 mL) to pH 5. A white solid separated, and was collected by filtration and washed with water. The combined filtrate and washings were acidified by adding further 2M hydrochloric acid to pH 1 and the solution was extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried with magnesium sulphate and evaporated to give 4-(1-(4-cyanobenzyl)piperidin-4-ylcarbamoyl)benzoic acid (0.718 g, 83%). LCMS (m/z): 364 (MH+).

Aufarbeitung

  1. customA white solid separated
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. additionby adding further 2M hydrochloric acid to pH 1
  5. extractionthe solution was extracted three times with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried with magnesium sulphate
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-78525b7e14824e57b00cb186100dc113
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255085B2

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