Triethylamine → Sulpiride

HRID 1733663Notes

Reaction equation

HRID 1733663 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.C(N(CC)CC)C.CS(ON1C2C=CC=CC=2N=N1)(=O)=O.[CH2:37]([N:39]1[CH2:43][CH2:42][CH2:41][CH:40]1[CH2:44][NH2:45])[CH3:38]>O1CCCC1>[CH2:37]([N:39]1[CH2:43][CH2:42][CH2:41][CH:40]1[CH2:44][NH:45][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:10]=[CH:11][C:3]=1[O:2][CH3:1])[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 896012-Methoxy-5-sulfamoylbenzoic acidHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 11745953Methanesulfonic acid, 1H-benzotriazol-1-yl ester

Product 1

HCID 5355SulpirideYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxy-5-sulfamoylbenzoic acid (2.3 g) and triethylamine (1.4 ml) are dissolved in anhydrous tetrahydrofuran (20 ml), and therto is added 1-methanesulfonyloxy-1,2,3-benzotriazole (2.2 g). After stirring at room temperature for 20 minutes, to the mixture is added 1-ethyl-2-aminomethylpyrrolidine (1.3 g) to precipitate oily products with exotherm. The mixture is stirred for 1 hour and then the solvent is distilled off. The resulting oily residue is dissolved in 1 N hydrochloric acid and the solution is washed twice with ethyl acetate. The aqueous layer is distilled under a reduced pressure to remove the remaining ethyl acetate and made alkaline with aqueous ammonia. The resulting precipitates are separated by filtration, washed with diluted aqueous ammonia and dried to give 1-ethyl-2-(2-methoxy-5-sulfamoylbenzamidomethyl)pyrrolidine (2.2 g), melting point: 175°-177° C.

Workup

  1. customto precipitate oily products with exotherm
  2. stirringThe mixture is stirred for 1 hour
  3. distillationthe solvent is distilled off
  4. dissolutionThe resulting oily residue is dissolved in 1 N hydrochloric acid
  5. washthe solution is washed twice with ethyl acetate
  6. distillationThe aqueous layer is distilled under a reduced pressure
  7. customto remove the remaining ethyl acetate
  8. customThe resulting precipitates
  9. customare separated by filtration
  10. washwashed with diluted aqueous ammonia
  11. customdried

Sources & evidence

ORD record
ord-f716d1dc6aa7410abaa7d231330bf760
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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