Triethylamine → 3,3-Dimethyl-1-[2-(6-phenylhexanoyl)-perhydropyridazinyl]pentane-1,2-dione

HRID 2228457Notes

Reaction equation

HRID 2228457 reaction equation
C(N([CH2:6][CH3:7])CC)C.ClC([O:11][CH2:12][CH:13]([CH3:15])C)=O.[CH3:16][C:17]([CH3:30])([CH2:28][CH3:29])[C:18](=[O:27])[C:19]([CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][NH:22]1)=[O:20]>C(Cl)Cl>[CH3:16][C:17]([CH3:30])([CH2:28][CH3:29])[C:18](=[O:27])[C:19]([CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][N:22]1[C:12](=[O:11])[CH2:13][CH2:15][CH2:24][CH2:25][CH2:26][C:7]1[CH:6]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 694178043,3-Dimethyl-1-perhydropyridazinylpentane-1,2-dione

Product 1

HCID 184700683,3-Dimethyl-1-[2-(6-phenylhexanoyl)-perhydropyridazinyl]pentane-1,2-dioneYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-phenylvalaric acid (0.2 g, 1.1 mmol) in 3 ml CH2Cl2 was added triethylamine (0.15 ml, 1.1 mmol), followed by isobutyl chloroformate (0.15 g, 1.1 mmol) at 0° C. After stirring for 5 minutes, a solution of 3,3-dimethyl-1-perhydropyridazinylpentane-1,2-dione (0.212 g, 1 mmol) in 1 ml CH2Cl2 was added. The reaction was gradually warmed up to room temperature. The crude material was subject to silica gel purification to yield final product as clear oil (0.20 g, 55%). Rf=0.58 (33% EtOAc/hexane). 1H NMR (CDCl3, 400 MHz): δ 0.89 (t, 3H, J=7.5); 1.24 (s, 6H); 1.37 (m, 2H); 1.68 (m, 6H); 1.74 (m, 4H); 2.23 (m, 2H); 2.62 (t, 2H, J=7.60); 2.80 (m, 2H); 4.53 (m, 2H); 7.21 (m, 5H). Anal. Calcd. for C23H24N2O3: C, 71.47; H, 8.87; N, 7.25. Found: C, 71.54; H, 8.80; N, 7.32.

Workup

  1. customThe crude material was subject to silica gel purification

Sources & evidence

ORD record
ord-d19e15624d2d428fbe3c0acdcc27ce3c
Source dataset
uspto-grants-2002_07
Patent number
US06417189B1

Reaction notes

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