1-Pyrrolidineethanamine → HCID 18367626, compound

HRID 1662835Notes

Reaction equation

HRID 1662835 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[N:12]1([CH2:17][CH2:18][NH2:19])[CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 17943m-Bromobenzenesulphonyl chloride

Product 1

HCID 18367626HCID 18367626, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromobenzene-1-sulfonyl chloride (1.29 g, 5.05 mmol) in 25 mL THF was charged with 2-(pyrrolidin-1-yl)ethanamine (0.6 mL, 5.05 mmol), and TEA (2.2 mL, 15.7 mmol) and allowed to stir for 1 hr. The reaction was quenched with 25 mL NaHCO3 (sat., aq.) and extracted with DCM (2×100 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by gradient flash chromatography (0 to 20% MeOH in DCM) to afford the title compound as a white solid (816 mg, 48%).

Workup

  1. customThe reaction was quenched with 25 mL NaHCO3 (sat., aq.)
  2. extractionextracted with DCM (2×100 mL)
  3. washThe combined organic layers were washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by gradient flash chromatography (0 to 20% MeOH in DCM)

Sources & evidence

ORD record
ord-7bee58f77f4f48289ee2a926b7442137
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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