Octylamine → 3-Isopropyl-2-oxopyrrolidine-3-carbonitrile

HRID 714786Notes

Reaction equation

HRID 714786 reaction equation
FC1C=CC(C([N:8]2[CH2:12][CH2:11][C:10]([CH:15]([CH3:17])[CH3:16])([C:13]#[N:14])[C:9]2=[O:18])=O)=CC=1.C(N)CCCCCCC>O1CCCC1>[CH:15]([C:10]1([C:13]#[N:14])[CH2:11][CH2:12][NH:8][C:9]1=[O:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 8143Octylamine2×HCID 1178410181-(4-Fluorobenzoyl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile

Product 1

HCID 916186363-Isopropyl-2-oxopyrrolidine-3-carbonitrileYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-fluorobenzoyl)-3-isopropyl-2-oxopyrrolidine-3-carbonitrile (280 mg) obtained in Step A in tetrahydrofuran (3 mL) was added n-octylamine (180 μL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added n-octylamine (168 μL) at room temperature, and the mixture was stirred at 50° C. for 5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (120 mg).

Workup

  1. stirringthe mixture was stirred at 50° C. for 5 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-854a9cd6dec44fe787917eeb4ca96692
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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