Water → N-{2-[4-(1-methylpropoxy)phenoxy]ethyl}phthalimide

HRID 2309839Notes

Reaction equation

HRID 2309839 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].O>CN(C=O)C>[CH3:1][CH:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:20][CH2:21][N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])=[CH:10][CH:11]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 138820044-(1-Methyl-1-propyloxy)-phenol

Product 1

HCID 20184869N-{2-[4-(1-methylpropoxy)phenoxy]ethyl}phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 4-(1-methylpropoxy)phenol (44.3 mmol) in 25 ml of DMF is added, under N2, potassium carbonate (51.0 mmol) followed by dropwise addition of N-(bromoethyl)phthalimide (51.0 mmol) in 30 ml of DMF. The mixture is stirred at RT overnight. Water is then added and the aqueous phase is extracted with ether. The combined organic layers are washed with 5% sodium hydroxide, with water and with brine, dried and the solent removed to give N-{2-[4-(1-methylpropoxy)phenoxy]ethyl}phthalimide. Following the procedures of Example 7, the above phthalimide (5.7 mmol) is reacted with hydrazine hydrate (5.7 mmol) to give 2-[4-(1-methylpropoxy)phenoxy]ethylamine.

Workup

  1. extractionthe aqueous phase is extracted with ether
  2. washThe combined organic layers are washed with 5% sodium hydroxide, with water and with brine
  3. customdried
  4. customthe solent removed

Sources & evidence

ORD record
ord-6c0f1e7c36e74c119ccecb06ee6ae215
Source dataset
uspto-grants-1987_09
Patent number
US04697033

Reaction notes

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