(3-Phenoxypropyl)amine → Dimethyl 2,6-dimethyl-4-[5-nitro-2-[4-[(3-phenoxypropyl)amino]butoxy]phenyl]pyridine3,5-dicarboxylate

HRID 1905397Notes

Reaction equation

HRID 1905397 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[O:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)[C:5]([C:27]([O:29][CH3:30])=[O:28])=[C:4]([CH3:31])[N:3]=1.[O:32]([CH2:39][CH2:40][CH2:41][NH2:42])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(#N)C>[CH3:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[O:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:42][CH2:41][CH2:40][CH2:39][O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:5]([C:27]([O:29][CH3:30])=[O:28])=[C:4]([CH3:31])[N:3]=1

Participants

4

Reactant 2

HCID 418237(3-Phenoxypropyl)amineHCID 14580316HCID 14580316, compound

Product 1

HCID 14580326Dimethyl 2,6-dimethyl-4-[5-nitro-2-[4-[(3-phenoxypropyl)amino]butoxy]phenyl]pyridine3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.22 g of dimethyl 2,6-dimethyl-4-[(4-bromobutoxy)-5-nitro-phenyl]pyridine-3,5-dicarboxylate and 1.4 g of 3-phenoxypropylamine were dissolved in 30 ml of acetonitrile and refluxed with heating for two hours. After evaporating the solvent, the residue was subjected to silica gel column chromatography and eluted with chloroform - methanol (95:5) to give 1.8 g of caramel-like dimethyl 2,6-dimethyl-4-[5-nitro-2-[4-[(3-phenoxypropyl)amino]butoxy]phenyl]pyridine3,5-dicarboxylate. The compound thus obtained in 29 ml of ethanol was dissolved and to the solution was added a solution of 0.2 g of anhydrous oxalic acid in 5 ml of ethanol. The resultant solution was allowed to stand overnight at 4° C. The precipitated crystals were collected by filtration and recrystallized from ethanol to give 1.5 g of dimethyl 2,6-dimethyl-4-[5-nitro-2-[4-[(3-phenoxypropyl)amino]butoxy]phenyl]pyridine-3,5-dicarboxylate oxalate. This compound has the following physico-chemical properties:

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for two hours
  3. customAfter evaporating the solvent
  4. washeluted with chloroform - methanol (95:5)

Sources & evidence

ORD record
ord-094712e6fc1649489f0b8874e3bedcaa
Source dataset
uspto-grants-1989_06
Patent number
US04843085

Reaction notes

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