Dimethylamine → (4-tert-Butyl-6-chloro-pyridin-2-ylmethyl)-dimethylamine

HRID 1446721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446721
[CH3:1][NH:2][CH3:3].C(N(CC)C(C)C)(C)C.Br[CH2:14][C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([Cl:25])[N:16]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:21]([C:19]1[CH:18]=[C:17]([Cl:25])[N:16]=[C:15]([CH2:14][N:2]([CH3:3])[CH3:1])[CH:20]=1)([CH3:24])([CH3:23])[CH3:22]

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 866343052-Bromomethyl-4-tert-butyl-6-chloro-pyridine

Produkt 1

HCID 86634306(4-tert-Butyl-6-chloro-pyridin-2-ylmethyl)-dimethylamineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Stir a solution of 2N dimethylamine (9.00 mL, 18.08 mmol) in tetrahydrofuran, N,N-diisopropylethylamine (2.80 g, 3.80 mL, 21.69 mmol) while adding a solution of 2-bromomethyl-4-tert-butyl-6-chloro-pyridine (1.90 g, 7.23 mmol) in tetrahydrofuran (20 mL). Stir for 2.5 hours at ambient temperature, dilute the reaction with aqueous sodium bicarbonate (80 mL) and extract the aqueous layer with ethyl acetate (3×75 mL). Pool, desiccate, filter and concentrate the organics to yield the title compound (99%) (1.64 g, 7.23 mmol). MS(ES), m/z 227 (M+1).

Aufarbeitung

  1. additiondilute
  2. extractionextract the aqueous layer with ethyl acetate (3×75 mL)
  3. filtrationPool, desiccate, filter
  4. concentrationconcentrate the organics

Quellen und Nachweise

ORD-Eintrag
ord-5cecbaf63360435eb679e54c4cfb4e3c
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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