Ethenesulfonyl fluoride → N-[2-(Fluorosulfonyl)ethyl]-3,4-dimethoxy-N-methylphenethylamine

HRID 1195928Notes

Reaction equation

HRID 1195928 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:6][CH2:7][NH:8][CH3:9].[CH:15]([S:17]([F:20])(=[O:19])=[O:18])=[CH2:16]>CN(C=O)C>[F:20][S:17]([CH2:15][CH2:16][N:8]([CH2:7][CH2:6][C:5]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:9])(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 69612Ethenesulfonyl fluorideHCID 77039N-Methylhomoveratrylamine

Product 1

HCID 54276374N-[2-(Fluorosulfonyl)ethyl]-3,4-dimethoxy-N-methylphenethylamineYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction between 3,4-dimethoxy-N-methylphenethylamine (15 mmol) and ethenesulfonyl fluoride (1.65 mL, 19 mmol) was carried out in DMF (30 mL) at ambient temperature for 3 hours as described in Example 16. There was obtained an orange liquid which was crystallized from ether/methanol to afford the title compound as a yellow solid (0.14 g, 11% yield), mp 200°-204° C.

Workup

  1. customThere was obtained an orange liquid which
  2. customwas crystallized from ether/methanol

Sources & evidence

ORD record
ord-148cfe2c30c64190a703affad1b22852
Source dataset
uspto-grants-1992_05
Patent number
US05112866

Reaction notes

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