Benzylamine → 1-(1,1-dimethylethyl)-N-(phenylmethyl)-4-Piperidinamine

HRID 132043

Reaktionsgleichung

Reaktionsgleichung von HRID 132043
[C:1]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:12]([NH:19][CH:8]1[CH2:9][CH2:10][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 738401-tert-Butyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 226479391-(1,1-dimethylethyl)-N-(phenylmethyl)-4-PiperidinamineAusbeute 26,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 1-tert-butyl-4-oxopiperidine (3.6 g, 23.1), benzylamine (5.1 ml, 46.8 mmol), acetic acid (1.5 ml) and sodium triacetoxyborohydride (7.38 g, 34.8 mmol) was stirred at ambient for 2 days. Reaction mixture reduced in vacuo, residue partitioned between aqueous K2CO3 and EtOAc. The organic portion was dried (Na2SO4), filtered and reduced in vacuo. The residue was subjected to chromatography using CH2Cl2/MeOH/NH4OH (87/12/1)as the eluent to yield N-benzyl-1-tert-butylpiperidin-4-amine (1.5 g) (LC/MS: Rt 0.45, [M+H]+247).

Aufarbeitung

  1. customReaction mixture
  2. custompartitioned between aqueous K2CO3 and EtOAc
  3. dry with materialThe organic portion was dried (Na2SO4)
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-23e43cdf53e04893bc29912064ce5045
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07385059B2

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