Water → N-benzyl-N-(3-furylmethyl)-2-chloroethylamine

HRID 611061Notes

Reaction equation

HRID 611061 reaction equation
[CH2:1]([N:8]([CH2:12][C:13]1[CH:17]=[CH:16][O:15][CH:14]=1)[CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C1(C)C=CC(S([Cl:34])(=O)=O)=CC=1.O>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([N:8]([CH2:9][CH2:10][Cl:34])[CH2:12][C:13]1[CH:17]=[CH:16][O:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 183774232-(Benzyl-(3-furylmethyl)amino)ethanol

Product 1

HCID 18377420N-benzyl-N-(3-furylmethyl)-2-chloroethylamine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.397 g (1.716 mmol) of 2-[benzyl-(3-furylmethyl)amino]ethanol, 0.36 ml (2.6 mmol) of triethylamine and 10 mg of 4-dimethylaminopyridine in 30 ml of dichloromethane, 0.39 g (2.1 mmol) of p-toluenesulfonyl chloride was added at room temperature, followed by stirring at room temperature for 6 hours. The reaction mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1) to yield N-benzyl-N-(3-furylmethy)-2-chloroethylamine.

Workup

  1. extractionextracted with dichloromethane 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1)

Sources & evidence

ORD record
ord-89b37852aad34baa8c8e3711b0deaaf4
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

Loading…