Sodium Hydroxide → 3-Dipropylamino-5-(pyrrol-1-yl)chroman

HRID 1684718Notes

Reaction equation

HRID 1684718 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[NH2:15])[O:7][CH2:6]1)[CH2:2][CH3:3].CO[CH:21]1[CH2:25][CH2:24][CH:23](OC)O1.[OH-].[Na+]>C(O)(=O)C>[CH2:16]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[N:15]2[CH:21]=[CH:25][CH:24]=[CH:23]2)[O:7][CH2:6]1)[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 790982,5-DimethoxytetrahydrofuranHCID 190281333-Dipropylamino-5-aminochroman

Product 1

HCID 190282493-Dipropylamino-5-(pyrrol-1-yl)chroman

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Dipropylamino-5-aminochroman (Example 14; 0.60 g, 2.42 mmol) was dissolved in acetic acid (10 ml) and 2,5-dimethoxytetrahydrofuran (0.40 g, 3.0 mmol) was added. The solution was refluxed for 1 hour. The solution was neutralized with NaOH (aq.) and extracted with toluene. The organic phase was dried with sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel by elution with ethyl acetate/hexane 1:9 to give the title compound. 13C-NMR: 111.75 21.89 24.81 52.69 53.15 67.94 108.93 115.67 118.22 118.44 121.87 127.22 141.47 155.27

Workup

  1. temperatureThe solution was refluxed for 1 hour
  2. extractionextracted with toluene
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography on silica gel by elution with ethyl acetate/hexane 1:9

Sources & evidence

ORD record
ord-74bb3691fb284212b960a3f3dcf04c20
Source dataset
uspto-grants-1997_06
Patent number
US05641807

Reaction notes

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