Phenethylamine → HCID 3740335, compound

HRID 2407628Notes

Reaction equation

HRID 2407628 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN([CH2:15][CH3:16])CC.[S:17](Cl)(Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH2:8]([NH:9][S:17]([C:2]1[C:15]2[C:16](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:7][CH:1]=1)(=[O:19])=[O:18])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 24648Sulfuryl chloride

Product 1

HCID 3740335HCID 3740335, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-phenylethylamine (3.5 mmol, 1 eq) in 40 ml CH2Cl2 were consecutively added, Et3N (0.58 ml, 4.18 mmol, 1.2 eq) and the corresponding sulfonyl chloride (2-naphthalenesulfonyl chloride, 0.87 g, 3.84 mmol, 1.1 eq). The reaction was performed at room temperature during 4 h, until the total consumption of the starting material. Once the solvent was evaporated, the crude mixture was chromatographically purified over Al2O3 using Hexane/AcOEt (70:30) as the eluant. The final yield of the product obtained was 91%, and the purity ≧99% (expressed in % HPLC area).

Workup

  1. customThe reaction was performed at room temperature during 4 h, until the total consumption of the starting material
  2. customOnce the solvent was evaporated
  3. customthe crude mixture was chromatographically purified over Al2O3
  4. customThe final yield of the product obtained

Sources & evidence

ORD record
ord-019b34c0415649ceb3bde7444e6ee3da
Source dataset
uspto-grants-2014_08
Patent number
US08809584B2

Reaction notes

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