Toluene → (S)-(-)-2-((3-Bromo-2,6-dimethoxybenzamido)methyl)-1-ethylpyrrolidine hydrochloride

HRID 224421

Reaction equation

HRID 224421 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[C:7]([O:17][CH3:18])=[C:8]([C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[C:9]([OH:11])=O.C1(C)C=CC=CC=1.[NH2:26][CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][N:29]1[CH2:33][CH3:34]>C(C(C)=O)C.C(OCC)C>[ClH:3].[CH2:33]([N:29]1[CH2:30][CH2:31][CH2:32][CH:28]1[CH2:27][NH:26][C:9](=[O:11])[C:8]1[C:12]([O:15][CH3:16])=[CH:13][CH:14]=[C:6]([Br:5])[C:7]=1[O:17][CH3:18])[CH3:34]

Participants

7

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 27747443-Bromo-2,6-dimethoxybenzoic acid

Product 1

HCID 15565708(S)-(-)-2-((3-Bromo-2,6-dimethoxybenzamido)methyl)-1-ethylpyrrolidine hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

30 ml of thionyl chloride is added to 17.6 g (0.067 mol) of 3-bromo-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 9.23 g (0.072 mol) of 2-(aminomethyl)-1-ethylpyrrolidine in 50 ml of methyl ethyl ketone. After stirring for 30 minutes at room temperature 150 ml of ethyl ether is added. The obtained precipitate is filtered off, washed with ether and recrystallized twice from ethanol-isopropyl ether. Yield: 21.0 g, m.p. 182°-84° C. (first recrystallization). m.p. 184°-85° C. (second recrystallization).

Workup

  1. temperatureThe mixture is heated on a steam bath for 30 minutes
  2. customThe solvent and excess thionyl chloride is evaporated at reduced pressure
  3. dissolutionThe residue is dissolved in 50 ml of dry methyl ethyl ketone
  4. additionThe solution is added dropwise
  5. additionis added
  6. filtrationThe obtained precipitate is filtered off
  7. washwashed with ether
  8. customrecrystallized twice from ethanol-isopropyl ether
  9. customYield: 21.0 g, m.p. 182°-84° C. (first recrystallization)
  10. customm.p. 184°-85° C. (second recrystallization)

Sources & evidence

ORD record
ord-26f7e6a3387244f3ba271f5c15ea707f
Source dataset
uspto-grants-1980_11
Patent number
US04232037

Linked notes

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