Piperidine → HCID 13824738, compound

HRID 247122

Reaction equation

HRID 247122 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]1[N:15]=[C:14]([CH2:16][C:17]#[N:18])[O:13][N:12]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:19]([C:22]1[CH:23]=[C:24]([CH:34]=[CH:35][CH:36]=1)[CH:25]=[C:26]([C:31]([CH3:33])=[O:32])[C:27]([O:29][CH3:30])=[O:28])([O-:21])=[O:20].N1CCCCC1>C(O)C>[NH2:18][C:17]1[O:32][C:31]([CH3:33])=[C:26]([C:27]([O:29][CH3:30])=[O:28])[CH:25]([C:24]2[CH:34]=[CH:35][CH:36]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:16]=1[C:14]1[O:13][N:12]=[C:11]([CH2:10][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:9])[N:15]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1536427Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoateHCID 201612213-(N-benzyl-N-methylamino)methyl-5-cyanomethyl-1,2,4-oxadiazole

Product 1

HCID 13824738HCID 13824738, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 1.21 g of 3-(N-benzyl-N-methylamino)methyl-5-cyanomethyl-1,2,4-oxadiazole prepared in Example 95 and 1.25 g of methyl 2-(3-nitrobenzylidene)acetoacetate in 10 ml of ethanol was added 0.1 ml of piperidine. The reaction mixture was heated under reflux for 3 hours and then concentrated in vacuo. The residue was triturated with 10 ml of ethyl acetate and the insoluble crystals were collected by filtration. Treatment of a solution of this base in chloroform with etherial hydrogen chloride afforded 820 mg of methyl 2-amino-3-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-6-methyl-4-(3-nitrophenyl)-4H-pyran-5-carboxylate as pale yellow powder, m.p. 201.5° C. (decomp.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with 10 ml of ethyl acetate
  5. filtrationthe insoluble crystals were collected by filtration

Sources & evidence

ORD record
ord-cb81b37849fb4a55ae58188147952c0b
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Linked notes

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