Triethylamine → 1-(2H-1,3-Benzodioxol-5-yl)pyrrolidin-2-one

HRID 2412341Notes

Reaction equation

HRID 2412341 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[CH2:8]1[O:17][C:16]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[O:9]1.C(N(CC)CC)C.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.C(Cl)Cl.CCOCC>[O:17]1[C:16]2[CH:15]=[CH:14][C:12]([N:13]3[CH2:2][CH2:3][CH2:4][C:5]3=[O:6])=[CH:11][C:10]=2[O:9][CH2:8]1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 783704-Chlorobutyryl chlorideHCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 130503821-(2H-1,3-Benzodioxol-5-yl)pyrrolidin-2-one

Reagents, catalysts & solvents 4

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-Chlorobutyryl chloride (1095.5 g, 7.77 mole) was added at 10°-25° C. to a mixture of 3,4-(methylenedioxy)aniline (1000.0 g, 7.29 mole), triethylamine (749.0 g, 7.40 mole) and methylene chloride (25000 mL). After stirring for 18 hours at ambient temperature ether was added and the butyramide intermediate was filtered then reslurried in water. The damp butyramide was combined with methylene chloride (10 L), 50% w/w aqueous sodium hydroxide (2000.0 g, 25.0 mole) and benzyltriethylammonium chloride (50.0 g, 0.22 mole). After stirring for 2.5 hours at ambient temperature the mixture was diluted with water and the aqueous layer was then separated. The methylene chloride layer was washed with water, decolorized with Darco G-60 and Filtrol #19, then vacuum concentrated. Ether was added to the concentrate. The mixture was chilled and the solids were collected and recrystallized from methylene chloride/ether giving 2245.0 g (75), m.p. 89°-91° which was one spot on tlc analysis.

Workup

  1. additionwas added
  2. filtrationthe butyramide intermediate was filtered
  3. customthe aqueous layer was then separated
  4. washThe methylene chloride layer was washed with water
  5. concentrationvacuum concentrated
  6. additionEther was added to the concentrate
  7. temperatureThe mixture was chilled
  8. customthe solids were collected
  9. customrecrystallized from methylene chloride/ether giving 2245.0 g (75), m.p. 89°-91° which

Sources & evidence

ORD record
ord-87237b7127984211bfc65a9a1d0fdc33
Source dataset
uspto-grants-1985_01
Patent number
US04491591

Reaction notes

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