2-(Dimethylamino)ethanol → 2-(N,N-dimethylamino)-ethyl 1-pyrrolidineacetate

HRID 5509

Reaction equation

HRID 5509 reaction equation
[N:1]1([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:14][N:15](CCO)[CH3:16]>>[N:1]1([CH2:6][C:7]([O:9][CH2:10][CH2:11][N:15]([CH3:16])[CH3:14])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 2109961-Pyrrolidineacetic acid, ethyl ester

Product 1

HCID 543299652-(N,N-dimethylamino)-ethyl 1-pyrrolidineacetate

Conditions

Temperature
150 °C

Procedure

To a mixture of 80 g (0.51 mol) of ethyl 1-pyrrolidineacetate and 0.5 g of sodium hydride (in the form of a 60% by weight suspension in mineral oil) was added 48 g (0.54 mol) of 2-(N,N-dimethylamino)ethanol. The mixture was purged with nitrogen gas, heated gradually and then maintained at about 150° C. while collecting the ethanol by-product in a Dean-Stark trap. The liquid reaction product was distilled at 85° C. at a pressure of 100 μmHg to provide 2-(N,N-dimethylamino)-ethyl 1-pyrrolidineacetate. The structure of the product was confirmed by nuclear magnetic resonance and infrared spectral analysis.

Workup

  1. customThe mixture was purged with nitrogen gas
  2. temperatureheated gradually
  3. customwhile collecting the ethanol by-product in a Dean-Stark trap
  4. customThe liquid reaction product
  5. distillationwas distilled at 85° C. at a pressure of 100 μmHg

Sources & evidence

ORD record
ord-f0f08fb4c13d448a91c7baff3cb35ade
Source dataset
uspto-grants-1993_09
Patent number
US05244997

Linked notes

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