HCID 13432892, compound → HCID 14668282, compound

HRID 2255518Notes

Reaction equation

HRID 2255518 reaction equation
[Cl-].[Br:2][C:3]1[C:4]([O:16][CH3:17])=[C:5]([C:9]([O:14][CH3:15])=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6]([NH2:8])=[O:7].C([N:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:42]N)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[Br:2][C:3]1[C:4]([O:16][CH3:17])=[C:5]([C:9]([O:14][CH3:15])=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6]([NH:8][CH2:42][C@@H:38]1[CH2:39][CH2:40][CH2:41][NH:37]1)=[O:7]

Participants

4

Reactant 2

HCID 13432892HCID 13432892, compoundHCID 19738270HCID 19738270, compound

Product 1

HCID 14668282HCID 14668282, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Bromo-2,5,6-trimethoxybenzamide chloride (1.48 g, 4.8 mmol) was reacted with (S)-(-)-1-trityl-2-aminomethylpyrrolidine (1.51 g, 4.4 mmol) in 10 ml dichloromethane at room temperature for 1 h. The solvent was evaporated and the residue was treated with 10 ml ethanol and 0.1 ml conc. HCl during 1 h. After evaporation the residue was partitioned between 0.5M HCl and Et2O. The aqueous phase was made alkaline, extracted with dichloromethane, dried (Na2SO4) and evaporated to give 1.30 g (79%) (S)-(+)-3-bromo-N-(2-pyrrolidinylmethyl)-2,5,6-trimethoxybenzamide. An analytical sample of the hydrochloride was prepared. M.p. 181°-182° C. (EtOH/acetone/Et2O).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with 10 ml ethanol and 0.1 ml conc. HCl during 1 h
  3. customAfter evaporation the residue
  4. customwas partitioned between 0.5M HCl and Et2O
  5. extractionextracted with dichloromethane
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-000b0ad97e1944e8b5eebdf4792ba6cb
Source dataset
uspto-grants-1993_08
Patent number
US05240957

Reaction notes

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