Hexane → Benzo[1,3]dioxol-5-ylmethyl-(5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-(3-ethoxy-benzyl)-amine

HRID 457366

Reaktionsgleichung

Reaktionsgleichung von HRID 457366
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)[CH3:2].[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH2:21][NH:22][CH2:23][C:24]3[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[C:28]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:27]=[N:26][C:25]=3[Cl:40])=[CH:20][C:15]=2[O:14][CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CCCCCC>CC(O)=O.CCOC(C)=O>[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH2:21][N:22]([CH2:23][C:24]3[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[C:28]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:27]=[N:26][C:25]=3[Cl:40])[CH2:7][C:6]3[CH:9]=[CH:10][CH:11]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)=[CH:20][C:15]=2[O:14][CH2:13]1

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 899083-EthoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18438149Benzo[1,3]dioxol-5-ylmethyl (5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-amine

Produkt 1

HCID 18437597Benzo[1,3]dioxol-5-ylmethyl-(5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-(3-ethoxy-benzyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-Ethoxybenzaldehyde (0.062 ml, 0.44 mmol) is added to a solution of benzo[1,3]dioxol-5-ylmethyl-(5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-amine) (0.045 g, 0.1 mmol) in CH2ClCH2Cl (5 mL) and HOAc (0.5 mL). The mixture is stirred at room temperature for 45 minutes, NaBH(OAc)3 (0.140 g, 0.66 mmol) is then added and the mixture is stirred over night. The solvent is removed in vacuo, the residue is partitioned between saturated aqueous NaHCO3 solution (20 mL) and EtOAc (20 mL), the organic layer is washed with water (15 mL), brine (15 mL), and then dried (Na2SO4). Evaporation of the solvent in vacuo provides the product shown above as a yellow oil. Preparative TLC (3:1 Hexane, EtOAc) of the residue provides purified product as a light yellow oil. LC-MS (M+1) 544. 1H NMR (δ, CDCl3) 7.36–7.48 (m, 5H), 7.18 (t, J=7.2 Hz, 1H), 6.70–6.87 (m, 6H), 5.91 (s, 2H), 4.00 (q, J=7.0 Hz, 2H), 3.80 (s, 2H), 3.56 (s, 2H), 3.52 (s, 2H), 2.70 (t, J=7.5 Hz, 2H), 1.41 (t, J=7.2 Hz, 2H), 0.84–1.02 (m, 4H), 0.58 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. stirringthe mixture is stirred over night
  2. customThe solvent is removed in vacuo
  3. customthe residue is partitioned between saturated aqueous NaHCO3 solution (20 mL) and EtOAc (20 mL)
  4. washthe organic layer is washed with water (15 mL), brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent in vacuo
  7. customprovides the product
  8. custompurified product as a light yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-9702c61f8b384733ab8f00dda36a8e1a
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186734B2

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