Reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:8]=1[C:9]([OH:11])=O.C1(C)C=CC=CC=1.[NH2:25][CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:32][CH3:33]>CC(CC)=O>[ClH:3].[CH2:32]([N:28]1[CH2:29][CH2:30][CH2:31][CH:27]1[CH2:26][NH:25][C:9](=[O:11])[C:8]1[C:12]([O:16][CH3:17])=[CH:13][CH:14]=[CH:15][C:7]=1[O:6][CH3:5])[CH3:33]Participants
6
Procedure
30 ml of thionyl chloride is added to 18.2 g (0.1 mol) of 2,6-dimethoxybenzoic acid. The mixture is heated on a steam bath for 30 minutes. To the solution is added 50 ml of toluene. The solvent and excess thionyl chloride is evaporated at reduced pressure. The residue is dissolved in 50 ml of dry methyl ethyl ketone. The solution is added dropwise while stirring to 12.8 g (0.1 mol) of 2-(aminomethyl)-1-ethyl-pyrrolidine in 50 ml methylethyl ketone. After the addition the mixture is stirred for 30 minutes at room temperature. The obtained precipitate is filtered off, washed with ether and recrystallized from ethanol - isopropyl ether. Yield: 26.7 g, m.p. 182°-84° C.
Workup
- temperatureThe mixture is heated on a steam bath for 30 minutes
- customThe solvent and excess thionyl chloride is evaporated at reduced pressure
- dissolutionThe residue is dissolved in 50 ml of dry methyl ethyl ketone
- additionThe solution is added dropwise
- additionAfter the addition the mixture
- filtrationThe obtained precipitate is filtered off
- washwashed with ether
- customrecrystallized from ethanol - isopropyl ether
Sources & evidence
- ORD record
- ord-7acfa7c2db2a4f08802a8102cb5cfeb8
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04232037
Linked notes
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