Methanol → HCID 9826160, compound

HRID 1279699Notes

Reaction equation

HRID 1279699 reaction equation
[C:1]1([CH:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16]([O:23][CH2:24][CH2:25][NH:26][CH:27]=O)=[CH:17][CH:18]=[CH:19][C:20]=53)=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>C1COCC1>[CH3:27][NH:26][CH2:25][CH2:24][O:23][C:16]1[C:15]2[C:14]3[C:22]4=[C:10]([O:9][CH2:8][CH:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[N:21]4[C:20]=2[CH:19]=[CH:18][CH:17]=1)[CH:11]=[CH:12][CH:13]=3

Participants

4

Reactant 2

HCID 887MethanolHCID 9842431HCID 9842431, compound

Product 1

HCID 9826160HCID 9826160, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]ethylformamide (0.769 g, 2.06 mmol) in dry THF (10 mL) is added borane-methylsulfide complex (0.59 mL, 6.2 mmol). The mixture is refluxed at 85° C. under an argon atmosphere for 19.5 h. The mixture is then cooled to room temperature and methanol is slowly added until gas evolution ceased. The solvents are removed under vacuum and methanol (10 mL) is added and then removed. The mixture is dissolved in methanol (15 mL), CH2C2 (5 mL) and conc. HCl (4 mL) and then heated at 65° C. for 1.5 h. The mixture is then neutralized with aqueous potassium carbonate and partitioned between water/CH2Cl2. The organic layer is washed with water, dried over magnesium sulfate and concentrated. Column chromatography (80 g silica gel) using CH2Cl2/hexane/CH3OH (80/17/3) as eluent gave N-methyl-2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine (0.536 g, 73%)

Workup

  1. additionis added borane-methylsulfide complex (0.59 mL, 6.2 mmol)
  2. temperatureThe mixture is then cooled to room temperature
  3. customThe solvents are removed under vacuum and methanol (10 mL)
  4. additionis added
  5. customremoved
  6. dissolutionThe mixture is dissolved in methanol (15 mL)
  7. temperatureCH2C2 (5 mL) and conc. HCl (4 mL) and then heated at 65° C. for 1.5 h
  8. custompartitioned between water/CH2Cl2
  9. washThe organic layer is washed with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-f88ce370c335469ba0be62166317c1e8
Source dataset
uspto-grants-2002_09
Patent number
US06448397B1

Reaction notes

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