Potassium Carbonate → 2-Chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehyde

HRID 2420972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2420972
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20]Cl)[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12].C([O-])([O-])=O.[K+].[K+]>C(O)CCC.O>[Cl:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 574347552-Chloro-4-(3-chloro-propoxy)-benzaldehyde

Produkt 1

HCID 575254242-Chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]benzaldehydeAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

N-Methylpiperazine (2.16 g, 21.5 mmol), 2-chloro-4-(3-chloro-propoxy)-benzaldehyde (3.19 g, 10.8 mmol), K2CO3 (4.46 g, 32.3 mmol), and KI (1.02 g, 5.38 mmol) were stirred in n-butanol (22 mL) at 90° C. for 18 h. The reaction mixture was diluted with water and then extracted three times with EtOAc. The combined extracts were dried (Na2SO4), filtered, and concentrated, yielding the crude product, which was purified by Method 1 to afford 2.04 g (63%) of an orange oil. 1H NMR (400 MHz, CD3OD): 10.3 (s, 1H), 7.86 (d, J=8.0, 1H), 7.08 (d, J=2.0, 1H), 7.00 (dd, J=8.0, 2.0, 1H), 4.15 (t, J=8.0, 2H), 3.00-2.30 (br s, 10H), 2.29 (s, 3H), 2.05-1.90 (m, 2H).

Aufarbeitung

  1. extractionextracted three times with EtOAc
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customyielding the crude product, which
  6. customwas purified by Method 1

Quellen und Nachweise

ORD-Eintrag
ord-1d28352e3a14467fafd5fbdda0bdb7e1
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956066B2

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