3-(Dimethylamino)-1-propanol → 3-(Dimethylamino)-propyl 7-benzoyl-5,10-dihydro-5-(3-methyl-2-butenyl)-1-phenazinecarboxylate

HRID 1857939Notes

Reaction equation

HRID 1857939 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]1[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][CH:15]=[CH:14][C:13]=1[N:12]2[CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][N:34]([CH3:39])[CH2:35]CCO.[Sn].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:1]([C:9]1[CH:10]=[C:11]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]1[C:17]([C:23]([O:25][CH2:26][CH2:27][CH2:33][N:34]([CH3:39])[CH3:35])=[O:24])=[CH:16][CH:15]=[CH:14][C:13]=1[N:12]2[CH2:28][CH:29]=[C:30]([CH3:31])[CH3:32])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 766463-(Dimethylamino)-1-propanol2×HCID 516892Sodium BicarbonateHCID 5352426Tin atomHCID 9802556HCID 9802556, compound

Product 1

HCID 221248843-(Dimethylamino)-propyl 7-benzoyl-5,10-dihydro-5-(3-methyl-2-butenyl)-1-phenazinecarboxylateYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In toluene (12 mL) was dissolved ethyl 7-benzoyl-5,10-dihydro-5-(3-methyl-2-butenyl)-1-phenazinecarboxylate (1.26 g, 2.95 mmol.) obtained in Example 2. To the mixture were further added 3-(dimethylamino)-1-propanol (3.50 mL, 29.5 mmol.) and tetra-n-butyl-1-isothiocyanate-3-hydroxydistannoxane (SCN(n-Bu)2SnOSn(n-Bu)2OH; 329 mg, 0.591 mmol.). The mixture was stirred at 100° C. for 24 hours in the stream of gaseous nitrogen. The mixture was further stirred at 100° C. for 24 hours, after addition of 3-(dimethylamino)-1-propanol (1.50 mL) and the above-mentioned tin compound (329 mg, 0.591 mmol.). The reaction mixture was cooled to room temperature and poured into saturated aqueous sodium hydrogencarbonate solution. The aqueous mixture was then extracted with ethyl acetate. The extract was washed with two portions of saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The dried extract was placed under reduced pressure to distill the solvent off. The residue was purified by medium pressure column chromatography (CHCl3 /methanol=1/0→95/5), to give the desired compound (142 mg, 10%).

Workup

  1. customobtained in Example 2
  2. stirringThe mixture was further stirred at 100° C. for 24 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionThe aqueous mixture was then extracted with ethyl acetate
  5. washThe extract was washed with two portions of saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. extractionThe dried extract
  8. distillationto distill the solvent off
  9. customThe residue was purified by medium pressure column chromatography (CHCl3 /methanol=1/0→95/5)

Sources & evidence

ORD record
ord-fedd2dcb1e5e43b3bedaf0d4046257cb
Source dataset
uspto-grants-2000_11
Patent number
US06150363

Reaction notes

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