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

HRID 20305

Reaktionsgleichung

Reaktionsgleichung von HRID 20305
[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 (5.11 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-48e4777ee5c849119137dbc7f8327e03
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745638B2

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