4-Fluorobenzyl chloride → HCID 18933360, compound

HRID 1598383Notes

Reaction equation

HRID 1598383 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][O:12][CH3:13].[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>C(O)C>[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:9]([CH2:10][CH2:11][O:12][CH3:13])[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 96024-Fluorobenzyl chlorideHCID 53634568HCID 53634568, compound

Product 1

HCID 18933360HCID 18933360, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of N,N'-bis(methoxyethyl)-1,3-propanediamine (4.5 g, 23.9 mmol) in ethanol (100 ml) was added under ice-cooling a solution of p-fluorobenzyl chloride (2.8 g, 19.1 mmol) in ethanol (50 ml) and the mixture was stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and the resulting white oily substance was subjected to silica gel chromatography to obtain 2.3 g of the title compound as a colorless oily substance from the fraction from methylene chloride-methanol-aqueous ammonia. Yield=40%.

Workup

  1. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-043e36ea314e43cdb2f42718f7dbf71f
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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