Dimethylamine → 1-(4-(Diethoxymethyl)phenyl)-n,n,-dimethylmethanamine

HRID 1467719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467719
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH3:2].[CH3:16][NH:17][CH3:18].O.[BH4-].[Na+]>CO>[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:17]([CH3:18])[CH3:16])=[CH:7][CH:6]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 962WaterHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 230003481-(4-(Diethoxymethyl)phenyl)-n,n,-dimethylmethanamineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4-(diethoxymethyl)benzaldehyde (6.8 g, 32.69 mmol) and dimethylamine in 33 wt. % solution in water (9.25 g, 98 mmol) in methanol (200 mL) was stirred at room temperature for overnight. Sodium borohydride (1.85 g, 49 mmol) was added by portions with ice cooling. After the addition, the mixture was stirred at room temperature for 4 hr. The mixture was quenched with water (100 mL) and extracted with ethyl acetate (100 ml×3). The extract was dried over anhydrous sodium sulfate and concentrated to give crude title compound (7.0 g, yield 90%), which was used in the next step without further purification. LC-MS (ESI) m/z: 238 (M+1)+.

Aufarbeitung

  1. additionAfter the addition
  2. customThe mixture was quenched with water (100 mL)
  3. extractionextracted with ethyl acetate (100 ml×3)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b87c585fc551430cb0240ff88cfced65
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999987B2

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