Aniline → 3-Piperidinamine, N-phenyl-1-(phenylmethyl)-

HRID 988804

Reaktionsgleichung

Reaktionsgleichung von HRID 988804
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH3-]C#N.[Na+].[OH-].[K+]>CO.O>[CH2:2]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 6115AnilineHCID 14797Potassium HydroxideHCID 30849241-Benzyl-3-piperidone hydrochloride hydrateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 113914823-Piperidinamine, N-phenyl-1-(phenylmethyl)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyl-piperidin-3-one hydrochloride salt (2.02 g, 8.95 mmol), aniline (1.67 ml, 17.89 mmol) in MeOH (20 ml) at room temperature was added NaCNBH3 (1.8 g, 28.64 mmol) in several portions. The mixture was stirred over night. The mixture was taken up in 50 ml of water, the pH was increased to 12 with 2N KOH and extracted with CH2Cl2 (3×50 ml). Standard work-up of the organic solution provided 164 as a dried residue which was used in the next step without further purification. LRMS (calculated for C18H22N2) 266, found 266.

Aufarbeitung

  1. extractionextracted with CH2Cl2 (3×50 ml)

Quellen und Nachweise

ORD-Eintrag
ord-36728f653cf34f3484dfa3958aee4592
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635661B2

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