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

HRID 37654Notes

Reaction equation

HRID 37654 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-8ffda47fa00c4b12a1a6271460898719
Source dataset
uspto-grants-1995_05
Patent number
US05420151

Reaction notes

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