1-Cyclopentyl-2-aminomethylpyrrolidine → N-(1-cyclopentyl-2-pyrrolidylmethyl)-2-methoxy-3-isopropyl-5-sulphamoyl-6-methyl benzamide

HRID 652759Notes

Reaction equation

HRID 652759 reaction equation
[CH:1]1([N:6]2[CH2:10][CH2:9][CH2:8][CH:7]2[CH2:11][NH2:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:13][O:14][C:15]1[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][C:21]([S:27](=[O:30])(=[O:29])[NH2:28])=[C:20]([CH3:31])[C:16]=1[C:17](Cl)=[O:18]>CC(CC)=O>[CH:1]1([N:6]2[CH2:10][CH2:9][CH2:8][CH:7]2[CH2:11][NH:12][C:17](=[O:18])[C:16]2[C:20]([CH3:31])=[C:21]([S:27](=[O:30])(=[O:29])[NH2:28])[CH:22]=[C:23]([CH:24]([CH3:26])[CH3:25])[C:15]=2[O:14][CH3:13])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 198601501-Cyclopentyl-2-aminomethylpyrrolidineHCID 201968202-Methoxy-3-isopropyl-5-sulphamoyl-6-methylbenzoyl chloride

Product 1

HCID 20196882N-(1-cyclopentyl-2-pyrrolidylmethyl)-2-methoxy-3-isopropyl-5-sulphamoyl-6-methyl benzamideYield 17%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

3.4 g of 1-cyclopentyl-2-aminomethylpyrrolidine (0.020 mole) and 40 ml of methyl-ethyl-ketone are placed in a 250 flask fitted with an agitator, a thermometer and a dropping funnel. The mixture is cooled to about +10° C., then a solution of 5.5 g of 2-methoxy-3-isopropyl-5-sulphamoyl-6-methylbenzoyl chloride (0.018 mole) in 40 ml of methyl-ethyl-ketone is poured in drop by drop. The mixture is reacted 1 hour at room temperature, then the solvent is evaporated under vacuum and the residue dissolved in 100 ml of hydrochloric acid (density 1.18). An insoluble rubbery product is filtered off, and the filtrate is made alkaline with 15 ml of ammonia (density 0.91). The precipitate formed is filtered, washed with water then re-crystallised in 30 ml of ethyl acetate. The crystals are filtered, washed with a little solvent and dried in an oven at 50°046732772 C. 1.3 g (17%) of product is obtained, melting at 196° C.

Workup

  1. customfitted with an agitator
  2. temperatureThe mixture is cooled to about +10° C.
  3. customThe mixture is reacted 1 hour at room temperature
  4. customthe solvent is evaporated under vacuum
  5. dissolutionthe residue dissolved in 100 ml of hydrochloric acid (density 1.18)
  6. filtrationAn insoluble rubbery product is filtered off
  7. customThe precipitate formed
  8. filtrationis filtered
  9. washwashed with water
  10. customthen re-crystallised in 30 ml of ethyl acetate
  11. filtrationThe crystals are filtered
  12. washwashed with a little solvent
  13. customdried in an oven at 50°046732772 C

Sources & evidence

ORD record
ord-46074cffaa324333834e377629cb41ab
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

Loading…