Ethyl 4-piperidinecarboxylate → 1-[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester

HRID 1486720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1486720
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=O)[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[NH:19]1[CH2:29][CH2:28][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:26]([O:25][C:23]([CH:22]1[CH2:28][CH2:29][N:19]([CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:10]=2)[CH2:20][CH2:21]1)=[O:24])[CH3:27]

Komponenten

6

Edukt 4

HCID 70770Ethyl 4-piperidinecarboxylateHCID 516892Sodium BicarbonateHCID 23750934-chloro-N-(3-formylphenyl)benzamideHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 867065481-[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-N-(3-formyl-phenyl)-benzamide (2.1 g, 8.09 mmol), ethyl isonipecotate (1.53 g, 9.55 mmol) in DCM (45 mL) is treated with sodium triacetoxy borohydride (2.5 g, 11.2 mmol) in 5 portions over 20 min. and the reaction mixture is stirred for 18 h at RT. Aq. sat. NaHCO3 (20 mL) is added and the mixture is stirred for 30 min. The phases are separated and the aqueous phase is extracted twice with DCM (50 ml). The combined organic phases are dried over MgSO4 and evaporated. The title compound is obtained as a colorless solid (3.24 g, 98%); LC-MS A: tR=0.72 min; [M+H]+=401.01.

Aufarbeitung

  1. stirringthe mixture is stirred for 30 min
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted twice with DCM (50 ml)
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a6b022559d5d4fa896cf050db2c9f0fe
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428456B2

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