4-Toluenesulfonyl chloride → N-(2-chloroethyl)-N-(3-furylmethyl)-6-phenylhexylamine

HRID 611078Notes

Reaction equation

HRID 611078 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:9]O)=[CH:2]1.C(N(CC)CC)C.C1(C)C=CC(S([Cl:39])(=O)=O)=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[Cl:39][CH2:9][CH2:8][N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:6][C:3]1[CH:4]=[CH:5][O:1][CH:2]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 196001892-[(3-Furylmethyl)-(6-phenylhexyl)amino]ethanol

Product 1

HCID 19599937N-(2-chloroethyl)-N-(3-furylmethyl)-6-phenylhexylamine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.533 g (8.470 mmol) of 2-[(3-furylmethyl)-(6-phenylhexyl)amino]ethanol, 1.77 ml (12.7 mmol) of triethylamine and 30 mg of 4-dimethylaminopyridine in 50 ml of dichloromethane, 1.94 g (10.2 mmol) of p-toluenesulfonyl chloride was added at room temperature, followed by overnight stirring at room temperature. 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 the desired product.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1)

Sources & evidence

ORD record
ord-1146f59bd558434d942e3ba469a2a209
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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