Dipropylamine → HCID 22914414, compound

HRID 1378115Notes

Reaction equation

HRID 1378115 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].Cl[CH2:9][C:10]1[O:14][N:13]=[C:12]([CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[N:11]=1>C(Cl)Cl>[CH2:1]([N:4]([CH2:9][C:10]1[O:14][N:13]=[C:12]([CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[N:11]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 22914443HCID 22914443, compound

Product 1

HCID 22914414HCID 22914414, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

35.6 ml (260 mmol) of dipropylamine were added dropwise at room temperature to a solution of 36 g (130 mmol) of 2-(5-chloromethyl-1,2,4-oxadiazol-3-ylmethyl)-2,3-dihydro-1H-isoindole-1,3-dione in 300 ml of methylene chloride, whereupon the mixture was stirred at room temperature for 24 hours. The yellow solution was washed with sat. sodium hydrogen carbonate solution, dried with sodium sulfate, filtered and evaporated. The residue obtained was chromatographed (silica gel, methylene chloride/aqueous ammonia 19:1). There were obtained 38 g (85%) of 2-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-ylmethyl)-2,3-dihydro-1H-isoindol-1,3-dione as a beige oil, Rf=0.12 (silica gel, methylene chloride/aqueous ammonia 19:1).

Workup

  1. washThe yellow solution was washed with sat. sodium hydrogen carbonate solution
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customwas chromatographed (silica gel, methylene chloride/aqueous ammonia 19:1)

Sources & evidence

ORD record
ord-c207955a48c040c487411c276e1880c6
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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