Potassium Iodide → 3-[N-(4-Phthalimidobutyl)amino]-5-methoxychroman

HRID 1655972Notes

Reaction equation

HRID 1655972 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:12][CH3:13])[O:4][CH2:3]1.Br[CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:20]1(=[O:29])[N:19]([CH2:18][CH2:17][CH2:16][CH2:15][NH:1][CH:2]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[O:12][CH3:13])[O:4][CH2:3]2)[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]12

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 139289485-Methoxy-3,4-dihydro-2H-1-benzopyran-3-amine

Product 1

HCID 104298593-[N-(4-Phthalimidobutyl)amino]-5-methoxychromanYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In a round bottomed flask, 2.2 mmol of 3-amino-5-methoxychroman (described in Patent EP 279,150) are dissolved in 6 ml of dimethylformamide in the presence of 2.4 mmol of N-(4-bromobutyl)phthalimide, 6.6 mmol of potassium carbonate and a catalytic amount of potassium iodide. The mixture is left stirring at 60° C. for 6 hours. After cooling, the solvent is evaporated off and, after aqueous hydrolysis, the crude reaction mixture is extracted with dichloromethane. After washing, drying and evaporation of the organic phase, the expected product is obtained after purification by chromatography on a silica column (elution solvent: ether/petroleum ether, 5:95).

Workup

  1. waitThe mixture is left
  2. temperatureAfter cooling
  3. customthe solvent is evaporated off
  4. customafter aqueous hydrolysis
  5. customthe crude reaction mixture
  6. extractionis extracted with dichloromethane
  7. washAfter washing
  8. customdrying
  9. customevaporation of the organic phase

Sources & evidence

ORD record
ord-ae5d23a06a2d4ff59b1a8b7eed4b849f
Source dataset
uspto-grants-1993_10
Patent number
US05252578

Reaction notes

Loading…