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

HRID 457365Notes

Reaction equation

HRID 457365 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][CH2:12][C:13]3[C:18]([CH2:19][CH2:20][CH2:21][CH3:22])=[C:17]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:16]=[N:15][C:14]=3[Cl:29])=[CH:9][C:4]=2[O:3][CH2:2]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:44][CH2:45][CH2:46][CH2:47][CH2:48]C.[CH3:50][CH2:51][O:52][C:53](C)=[O:54]>CC(O)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([CH2:48][C:47]3[CH:46]=[CH:45][C:44]4[O:54][CH2:53][O:52][C:51]=4[CH:50]=3)[CH2:12][C:13]3[C:18]([CH2:19][CH2:20][CH2:21][CH3:22])=[C:17]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:16]=[N:15][C:14]=3[Cl:29])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 18438149Benzo[1,3]dioxol-5-ylmethyl (5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-amine

Product 1

HCID 18437486Bis-benzo[1,3]dioxol-5-ylmethyl-(5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Piperonyl (0.06 g, 0.4 mmol) is added to a solution of benzo[1,3]dioxol-5-ylmethyl-(5-butyl-3-chloro-6-phenyl-pyridazin-4-ylmethyl)-amine (0.042 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 (0.127 g, 0.6 mmol) is then added and the mixture is stirred overnight. The solvent is removed in vacuo, the residue is partitioned between saturated aqueous NaHCO3 solution (20 mL) and EtOAc (20 mL), and the organic layer is washed with water (15 mL), brine (15 mL), and then dried (Na2SO4). Evaporation of the solvent in vacuo provides the compound shown above as a yellow oil. Preparative TLC (3:1 Hexane, EtOAc) of the residue provides a light yellow oil. LC-MS (M+1) 544. 1H NMR (δ, CDCl3) 7.37–7.48 (m, 5H), 6.77 (s, 2H), 6.72 (s, 4H), 5.91 (s, 4H), 3.78 (s, 2H), 3.49 (s, 4H), 2.69 (t, J=7.2 Hz, 2H), 0.85–1.02 (m, 4H), 0.59 (t, J=7.0 Hz, 3H).

Workup

  1. stirringthe mixture is stirred overnight
  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 compound

Sources & evidence

ORD record
ord-6130d407674447f198121802ef32e3af
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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