Glutaric anhydride → HCID 11535623, compound

HRID 593232Notes

Reaction equation

HRID 593232 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH2:9]([NH2:12])[C:10]#[CH:11]>C(Cl)Cl>[O:6]=[C:5]([NH:12][CH2:9][C:10]#[CH:11])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 239041Propargylamine

Product 1

HCID 11535623HCID 11535623, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
43 °C

Procedure

Glutaric anhydride (2.34 g, 0.2 mmol) was dissolved in 100 ml dry DCM in a round bottom flask and degassed with Ar. Propargyl amine (1.4 ml, 20 mmol) was added and the reaction mixture was refluxed at 43° C. for 2 hours and then stirred at room temperature for 2 hours. The solvent was evaporated and the crude product was purified by column chromatography using 95:5 CH2Cl2/MeOH. Yield: 75%. 1H NMR (CDCl3, 200 MHz) δ (ppm): 1.67-1.76 (m, 2H), 2.09-2.26 (m, 4H), 2.38-2.41 (m, 1H), 3.75-3.76 (d, 2H).

Workup

  1. customdegassed with Ar
  2. customThe solvent was evaporated
  3. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6edf58ad4d184360849a3439a5e99b5b
Source dataset
uspto-grants-2016_01
Patent number
US09242010B2

Reaction notes

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