Benzyl Bromide → ethyl 2-[4-{N-(4-chlorophenyl)-N-benzylaminomethyl}phenoxy]-2-methylpropionate

HRID 2058096Notes

Reaction equation

HRID 2058096 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:10][C:11]1[CH:33]=[CH:32][C:14]([NH:15][CH2:16][C:17]2[CH:31]=[CH:30][C:20]([O:21][C:22]([CH3:29])([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:21][C:22]([CH3:28])([CH3:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:30][CH:31]=2)[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 20329859Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionate hydrochloride

Product 1

HCID 20329839ethyl 2-[4-{N-(4-chlorophenyl)-N-benzylaminomethyl}phenoxy]-2-methylpropionateYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3.47 g of benzyl bromide is added dropwise to a mixture of 6 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]-2-methylpropionate hydrochloride, 3.24 g of potassium carbonate and 90 ml of dimethylformamide, and the resulting mixture is stirred at 60° C. for 3 hours. The reaction mixture is poured into 300 ml of ice-water and is extracted three times with 100 ml of ethyl acetate and twice with 50 ml of the same. The extract is washed with a saturated aqueous solution of sodium chloride and then dried. The solvent is distilled off from the dried extract, and the residue (7.5 g) is purified by column chromatography with 150 g of silica gel, using chloroform as a developer, to give 5.7 g of ethyl 2-[4-{N-(4-chlorophenyl)-N-benzylaminomethyl}phenoxy]-2-methylpropionate. The product is dissolved in 100 ml of ether, and dried hydrogen chloride gas is introduced into the solution. The resulting crystals are collected by filtration and recrystallized from isopropyl alcohl to give 4.3 g of ethyl 2-[4-{N-(4-chlorophenyl)-N-benzylaminomethyl}phenoxy]-2-methylpropionate hydrochloride, mp 137° to 141° C.

Workup

  1. extractionis extracted three times with 100 ml of ethyl acetate
  2. washThe extract is washed with a saturated aqueous solution of sodium chloride
  3. customdried
  4. distillationThe solvent is distilled off from the dried
  5. extractionextract
  6. customthe residue (7.5 g) is purified by column chromatography with 150 g of silica gel

Sources & evidence

ORD record
ord-1ef056102b8a44fd9b1a55eb78d0fd3f
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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