Methylamine → HCID 22914390, compound

HRID 1378116Notes

Reaction equation

HRID 1378116 reaction equation
CN.[CH2:3]([N:6]([CH2:10][C:11]1[O:15][N:14]=[C:13]([CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)[N:12]=1)[CH2:7][CH2:8][CH3:9])[CH2:4][CH3:5]>C(O)C>[NH2:17][CH2:16][C:13]1[N:12]=[C:11]([CH2:10][N:6]([CH2:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH3:5])[O:15][N:14]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22914414HCID 22914414, compound

Product 1

HCID 22914390HCID 22914390, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

400 ml of methylamine (33% in ethanol) were added dropwise to a solution of 38 g (111 mmol) of 2-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-ylmethyl)-2,3-dihydro-1H-isoindol-1,3-dione in 300 ml of ethanol. The mixture was stirred at 70° for 1.5 hours and subsequently evaporated. The residue was triturated in methylene chloride and filtered off. The filtrate was concentrated and chromatographed (silica gel, methylene chloride/methanol 19:1). There were obtained 15.6 g (66%) of (3-aminomethyl-1,2,4-oxadiazol-5-ylmethyl)-dipropyl-amine as a yellow oil, Rf=0.25 (silica gel, methylene chloride/methanol 9:1).

Workup

  1. customsubsequently evaporated
  2. customThe residue was triturated in methylene chloride
  3. filtrationfiltered off
  4. concentrationThe filtrate was concentrated
  5. customchromatographed (silica gel, methylene chloride/methanol 19:1)

Sources & evidence

ORD record
ord-a46b50dd72fb490b9a7470d736ba2297
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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