Cyclopropylamine → HCID 53733396, compound

HRID 652755Notes

Reaction equation

HRID 652755 reaction equation
Cl[CH:2]([CH2:19][CH2:20][CH2:21]Cl)[CH2:3][NH:4][C:5](=[O:18])[C:6]1[CH:11]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:9]=[CH:8][C:7]=1[O:16][CH3:17].[CH:23]1([NH2:26])[CH2:25][CH2:24]1>O>[CH:23]1([N:26]2[CH2:21][CH2:20][CH2:19][CH:2]2[CH2:3][NH:4][C:5](=[O:18])[C:6]2[CH:11]=[C:10]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:9]=[CH:8][C:7]=2[O:16][CH3:17])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 30177965-(aminosulphonyl)-N-(2,5-dichloropentyl)-2-methoxybenzamide

Product 1

HCID 53733396HCID 53733396, compoundYield 189.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

36.9 g (0.1 mole) of N-(2,5-dichloropentyl)-2-methoxy-5-sulphamoyl-benzamide and 57 g of cyclopropylamine are placed in 250 ml bottle. They are brought to reflux for 6 hours, left to stand for 1 night then brought back to reflux for 5 hours. The suspension obtained is poured into 300 ml of water and 50 g of ice. The white precipitate is washed with water and dried in an oven at 60° C. It melts at 163° C. and weighs 29.5 g (83.6%). It is dissolved in 2 liters of acetonitrile and filtered in the presence of carbon black. The filtrate is left to crystallise. The crystals obtained are filtered, washed with acetonitrile and dried at 40° C. 67 g (yield 74.9%) of N-(1-cyclopropyl-2-pyrrolidinylmethyl)-2-methoxy-5-sulphamoylbenzamide is collected, melting at 180° C.

Workup

  1. temperatureto reflux for 6 hours
  2. waitleft
  3. waitto stand for 1 night
  4. temperatureto reflux for 5 hours
  5. customThe suspension obtained
  6. washThe white precipitate is washed with water
  7. customdried in an oven at 60° C
  8. dissolutionIt is dissolved in 2 liters of acetonitrile
  9. filtrationfiltered in the presence of carbon black
  10. waitThe filtrate is left
  11. customto crystallise
  12. customThe crystals obtained
  13. filtrationare filtered
  14. washwashed with acetonitrile
  15. customdried at 40° C

Sources & evidence

ORD record
ord-47a372a3f332498995b12b5025af0244
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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