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

HRID 1034269
Notes
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Reaction equation

HRID 1034269 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-7aab8da8aff34ec39a5b2301bfc633a9
Source dataset
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05314907

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes