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Water → 3-[N-Propyl-N-(4-phthalimidobutyl)amino]-5-methoxychroman

HRID 327529
Notes
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Reaction equation

HRID 327529 reaction equation
[C:1]1(=[O:28])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][CH:11]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:21][CH3:22])[O:13][CH2:12]2)[C:4](=[O:23])[C:3]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:2]12.I[CH2:30][CH2:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:30]([N:10]([CH:11]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[O:21][CH3:22])[O:13][CH2:12]1)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:4](=[O:23])[C:3]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:2]2[C:1]1=[O:28])[CH2:31][CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 104298593-[N-(4-Phthalimidobutyl)amino]-5-methoxychroman

Product 1

HCID 102516733-[N-Propyl-N-(4-phthalimidobutyl)amino]-5-methoxychromanYield 81%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

1.5 mmol of the compound prepared in Example 1 is dissolved in 10 ml of dimethylformamide in the presence of 4.4 mmol of 1-iodopropane and 4.4 mmol of potassium carbonate. After 24 hours' stirring at 60° C., the solvent is evaporated off and the crude reaction mixture is taken up with 10 ml of water and extracted with dichloromethane. The organic phase is dried and evaporated and the expected product is obtained after purification by chromatography on a silica column (elution solvent: ether/petroleum ether, 1:99).

Workup

  1. customthe solvent is evaporated off
  2. customthe crude reaction mixture
  3. extractionextracted with dichloromethane
  4. customThe organic phase is dried
  5. customevaporated

Sources & evidence

ORD record
ord-80248a739c7f4508a5df879234f94340
Source dataset
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05273994

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes