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

HRID 1643199Notes

Reaction equation

HRID 1643199 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, 04 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 Na44CO3 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 a 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 Na44CO3 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 a in vacuo
  7. customprovides the compound

Sources & evidence

ORD record
ord-e8c4431722e94167b46c5f5f77ec58bc
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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