Diethyl Ether → N-propionyl-3-(3-methoxyphenyl)pyrrolidone

HRID 2108191Notes

Reaction equation

HRID 2108191 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[C:21](Cl)(=[O:24])[CH2:22][CH3:23].CC[O:28]CC>>[C:21]([N:11]1[CH2:12][CH2:13][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:10]1=[O:28])(=[O:24])[CH2:22][CH3:23]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 129379913-(3-Methoxyphenyl)pyrrolidine

Product 1

HCID 23045623N-propionyl-3-(3-methoxyphenyl)pyrrolidoneYield 100%

Conditions

Temperature
0 °C

Procedure

3-(3-methoxyphenyl)pyrrolidine (8.86 g, 0.050 mol) and triethylamine (5.57 g, 0.055 mol) was dissolved in 500 ml of dry ether. The solution was cooled to 0° C and propionyl chloride (5.09 g, 0.055 mol) was added dropwise with stirring. The reaction mixture was then allowed to acquire ambient temperature, whereafter it was refluxed for 30 minutes. Triethylamine hydrochloride was filtered off, and the filtrate was evaporated leaving 11.7 g (100%) of crude N-propionyl-3-(3-methoxyphenyl)pyrrolidone, which was used in the next reaction step without further purification. The crude amide (11.7 g, 0.050 mol) was reduced with LiAlH4 (2.85 g, 0.075 mol) in refluxing ether (200 ml) for 24 hours. Workup of the reaction mixture afforded 10 g of product, which upon distillation in vacuo yielded 9.1 g (83%) of N-propyl-3-(3-methoxyphenyl)-pyrrolidine b.p. 85-86° C/O.1 mm Hg. MS: m/e 219 (M +, 12%) 190 (M--C2H5, 100%).

Workup

  1. customto acquire ambient temperature, whereafter it
  2. temperaturewas refluxed for 30 minutes
  3. filtrationTriethylamine hydrochloride was filtered off
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-1b24e25283af4c6594e8199604868eda
Source dataset
uspto-grants-1990_06
Patent number
US04937346

Reaction notes

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