Benzylamine → HCID 43654054, compound

HRID 505396Notes

Reaction equation

HRID 505396 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:9]([NH:16][S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chloride

Product 1

HCID 43654054HCID 43654054, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-chloro-propylsulfonyl chloride was added dropwise to a stirred solution of benzylamine (1 eq) and triethylamine (1.1 eq) in DCM (0.6 M) at 0° C. The solution was stirred at RT overnight. The solvent was then removed in vacuo, Et2O was added to get a precipitate that was eliminated by filtration, while the filtrate was concentrated in vacuo. Subsequent addition of PE resulted in the formation of a white precipitate that was collected by filtration to afford the title compound (86%). 1H NMR (400 MHz, DMSO-d6, 300 K) δ 2.02-2.09 (m, 2H), 3.03-3.07 (m, 2H), 3.67 (t, J 6.6, 2H), 4.14 (d, J 6.1, 2H), 7.25-7.30 (m, 1H), 7.32-7.36 (m, 4H), 7.73 (t, J 6.1, 1H).

Workup

  1. customThe solvent was then removed in vacuo, Et2O
  2. additionwas added
  3. customto get a precipitate that
  4. filtrationwas eliminated by filtration, while the filtrate
  5. concentrationwas concentrated in vacuo
  6. additionSubsequent addition of PE
  7. customresulted in the formation of a white precipitate that
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-bb4b26eeee8f4b758bfbe61583447e48
Source dataset
uspto-grants-2010_08
Patent number
US07781422B2

Reaction notes

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