N-Methylbenzylamine → 3-(N-benzyl-N-methylamino)methyl-5-cyanomethyl-1,2,4-oxadiazole

HRID 247120Notes

Reaction equation

HRID 247120 reaction equation
C1C2[CH:6]([C:8]3[O:12][N:11]=[C:10](N)[N:9]=3)[CH2:7][N:3](C2)C1.[CH3:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:23](N(CC)CC)C>C1COCC1>[CH2:16]([N:15]([CH2:23][C:10]1[N:9]=[C:8]([CH2:6][C:7]#[N:3])[O:12][N:11]=1)[CH3:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 1639383-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane

Product 1

HCID 201612213-(N-benzyl-N-methylamino)methyl-5-cyanomethyl-1,2,4-oxadiazoleYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 8.0 g of the oxadiazole prepared above, 9.26 g of N-methylbenzylamine and 10.32 g of triethylamine in 50 ml of THF was allowed to stand at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The resultant solution was washed with water, dried and evaporated in vacuo. The residue was chromatographed on silica gel using benzeneethyl acetate (2:1) as eluent to give 5.56 g of 3-(N-benzyl-N-methylamino)methyl-5-cyanomethyl-1,2,4-oxadiazole as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe resultant solution was washed with water
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel using benzeneethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-d472f0b3857543bf941249551c0b37ea
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

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