2-(Methylamino)ethanol → N-(2-hydroxyethyl)-N-methyl-1-pyrrolidinecarboxamide

HRID 1110384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110384
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[N:13]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1>ClC(Cl)Cl>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[C:18]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:19]

Komponenten

5

Edukt 3

HCID 80162-(Methylamino)ethanol2×HCID 8471TriethylamineHCID 709371-Pyrrolidinecarbonyl chloride

Produkt 1

HCID 15078442N-(2-hydroxyethyl)-N-methyl-1-pyrrolidinecarboxamideAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 7.5 parts of 2-(methylamino)ethanol in 75 parts of trichloromethane were added 9.8 parts of N,N-diethylethanamine while cooling in an ice bath. A solution of 13.4 parts of 1pyrrolidinecarbonyl chloride in 52.5 parts of trichloromethane was added dropwise (exothermic reaction, the temperature rose from -10° C. to ~0° C.). Upon complete addition, stirring was continued for 6 hours at room temperature. Another portion of 1.5 parts of 2-(methylamino)ethanol was added and stirring was continued over weekend at room temperature. The separated organic layer was washed with a hydrochloric acid solution 5% and water, dried, filtered and evaporated, yielding 7 parts (40.1%) of N-(2-hydroxyethyl)-N-methyl-1-pyrrolidinecarboxamide as a residue (int. 30).

Aufarbeitung

  1. temperaturewhile cooling in an ice bath
  2. customexothermic reaction
  3. customrose from -10° C. to ~0° C.
  4. additionUpon complete addition
  5. stirringstirring
  6. waitwas continued over weekend at room temperature
  7. washThe separated organic layer was washed with a hydrochloric acid solution 5% and water
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-bed7d5129fd24e5d8da0fde209bfae88
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04975439

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