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

HRID 2226179Notes

Reaction equation

HRID 2226179 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-1c2525146e934675a8bc4cf968061a57
Source dataset
uspto-grants-1994_09
Patent number
US05346916

Reaction notes

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