1-Pyrrolidineethanamine → 4-Bromo-N-(2-(pyrrolidin-1-yl)ethyl)benzenesulfonamide

HRID 1662841Notes

Reaction equation

HRID 1662841 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:12]1([CH2:17][CH2:18][NH2:19])[CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:19][CH2:18][CH2:17][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 40330904-Bromo-N-(2-(pyrrolidin-1-yl)ethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-bromo-benzenesulfonyl chloride (3.36 g, 13.1 mmol, 1 equiv) was dissolved in 50 mL DCM and treated with TEA (9.16 mL, 65.7 mmol, 5 equiv). To this, while stirring the solution, was added 2-pyrrolidin-1-yl-ethylamine (3 g, 26.3 mmol, 2 equiv). After 3 h, reaction was poured onto DCM/water mixture and washed once. The aqueous phase was back extracted once with fresh DCM. Organic phases were combined, washed once with brine and dried over sodium sulfate. Filtration followed by rotary evaporation provided desired product. White needles (3.92 g, 90%). Rf=0.35 (10% MeOH/DCM)

Workup

  1. customreaction
  2. additionwas poured onto DCM/water mixture
  3. washwashed once
  4. extractionThe aqueous phase was back extracted once with fresh DCM
  5. washwashed once with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration
  8. customfollowed by rotary evaporation

Sources & evidence

ORD record
ord-4310882213e14eadb75cc5f7eceb5e38
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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