Water → N-(4-((6-chloro-2-pyridinyl)oxy)phenyl)-2,5-dimethyl-1-pyrrolidine carboxamide
Reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH3:7])[NH:3]1.[Cl:8][C:9]1[N:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]=[C:23]=S)=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1.[OH2:31]>>[Cl:8][C:9]1[N:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([N:3]3[CH:4]([CH3:7])[CH2:5][CH2:6][CH:2]3[CH3:1])=[O:31])=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=1Participants
Procedure
2,5-Dimethylpyrrolidine (2.5 grams; 0.0284 mole) was added at ambient temperature to a solution of 4-((6-chloro-2-pyridinyl)oxy)phenyl isothiocyanate, prepared as in Example 7 (7.0 grams; 0.0284 moles) in 25 ml. of dry pyridine. The resulting reaction mixture was allowed to stand at ambient temperatures for a period of about 16 hours and then poured into 300 ml. of cold water. The resulting product precipitate was recovered by filtration, washed with water and taken up in boiling benzene. Hexane was then added to the solution and the solution cooled to precipitate the desired N-(4-((6-chloro-2-pyridinyl)oxy)phenyl)-2,5-dimethyl-1-pyrrolidine carboxamide compound as a crystalline solid having a carbon, hydrogen, nitrogen and chlorine content of 62.2, 5.7, 11.9 and 10.2 percent, respectively, as compared with contents of 62.5, 5.82, 12.5 and 10.25 percent, respectively, calculated for the named structure.
Workup
- customThe resulting reaction mixture
- additionpoured into 300 ml
- filtrationThe resulting product precipitate was recovered by filtration
- washwashed with water
- additionHexane was then added to the solution
- temperaturethe solution cooled
- customto precipitate the desired N-(4-((6-chloro-2-pyridinyl)oxy)phenyl)-2,5-dimethyl-1-pyrrolidine carboxamide compound as a crystalline solid
Sources & evidence
- ORD record
- ord-cf54832f49444fd48e57bcc126d25a92
- Source dataset
- uspto-grants-1977_12
- Patent number
- US04063928
Reaction notes
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