1-Pyrrolidineethanamine → HCID 70456219, compound

HRID 434349Notes

Reaction equation

HRID 434349 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([Cl:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>O>[Cl-:14].[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:15][CH2:16][CH2:17][NH+:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 8481N-Acetylsulfanilyl chloride

Product 1

HCID 70456219HCID 70456219, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Acetylaminobenzenesulphonylchloride (21.9 g) was added in portions to a solution of 1-(2-aminoethyl)pyrrolidine (10.7 g, 0.9 mol) in water (250 ml). The mixture was stirred for 9 hours at room temperature. At the end of the reaction, the solution has pH 6-7. A portion of the mixture (165 ml) was removed and adjusted to pH 9.5. The precipitate from the mixture (4.9 g) was removed under suction and dissolved in ethyl acetate (170 ml). The solution was filtered and HCl gas was passed through. Precipitated chloride was isolated and recrystallised from absolute ethanol (350 ml) to give the product (27.2 g).

Workup

  1. customAt the end of the reaction
  2. customA portion of the mixture (165 ml) was removed
  3. customThe precipitate from the mixture (4.9 g) was removed under suction
  4. dissolutiondissolved in ethyl acetate (170 ml)
  5. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-36a002f8a1804d1581bd5c71c6c1594f
Source dataset
uspto-grants-1983_08
Patent number
US04396622

Reaction notes

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