Hydrochloric Acid → HCID 177933, compound

HRID 2118543Notes

Reaction equation

HRID 2118543 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([O:10]C)=O.[NH2:12][CH2:13][C:14]12[CH2:21][CH2:20][CH2:19][N:18]1[CH2:17][CH2:16][CH2:15]2.Cl>>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([NH:12][CH2:13][C:14]12[CH2:21][CH2:20][CH2:19][N:18]1[CH2:17][CH2:16][CH2:15]2)=[O:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 108835Methyl 2-oxo-1-pyrrolidineacetateHCID 10654304(Hexahydro-1H-pyrrolizin-7A-YL)methanamine

Product 1

HCID 177933HCID 177933, compound

Conditions

Temperature
80 °C

Procedure

A mixture consisting of 14.1 g (89.6 mmol) of methyl 2-oxo-1-pyrrolidineacetate and 11.4 g (81.4 mmol) of 7a-(aminomethyl)pyrrolizidine was heated and stirred for 6 hours at 80° C. under argon atmospher. After cooling, the reaction mixture was then solved with 1.0N-hydrochloric acid and extracted 3 times with dichloromethane. An aqueous layer was rendered alkaline by the addition of sodium hydroxide solution and extracted 3 times with dichloromethane followed by drying over anhydrous magnesium sulfate. After removal of the drying agent through filtration, the solvent was evaporated under reduced pressure to obtain a yellowish oil as a free base of the desired compound. The free base was converted to terephthalate by usual manner. Yield: 32.0 g (91.1%).

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. extractionextracted 3 times with dichloromethane
  4. additionby the addition of sodium hydroxide solution
  5. extractionextracted 3 times with dichloromethane
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. customAfter removal of the drying agent
  8. filtrationthrough filtration
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c737d048556d4021bb12fa503bcad00a
Source dataset
uspto-grants-1987_07
Patent number
US04678801

Reaction notes

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