Potassium Carbonate → HCID 12148622, compound

HRID 1279688Notes

Reaction equation

HRID 1279688 reaction equation
[C:1]1([C@@H:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:20]3=[CH:19][CH:18]=[CH:17][C:16]=5[OH:23])=[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.Br[CH2:25][C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]1([C@@H:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16]([O:23][CH2:25][C:26]#[N:27])=[CH:17][CH:18]=[CH:19][C:20]=53)=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate3×HCID 11534Bromoacetonitrile3×HCID 12148621HCID 12148621, compound

Product 1

HCID 12148622HCID 12148622, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (S)-(+)-1-Phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol (0.161 g, 0.534 mmol), bromoacetonitrile (0.074 mL, 1.07 mmol), potassium carbonate (0.148 g, 1.07 mmol), and DMF (2 mL) is stirred at 70° C. for 4 h. Additional bromoacetonitrile (0.074 mL) and potassium carbonate (0.074 g) are then added and the mixture is stirred overnight. Bromoacetonitrile and potassium carbonate (0.074 mL and 0.074 g, respectively) are then added and the temperature is increased to 90° C. The mixture is heated at that temperature for 5.5 h and then allowed to cool and stir overnight, after which the mixture is partitioned between ethyl acetate, aq. ammonium chloride, and brine. The organic layers are dried over magnesium sulfate, concentrated, and the residue is chromatographed on silica gel gel (40 mL) using first CH2Cl2/hexane (1:1) to elute unreacted starting material, and then ethyl acetate/CH2Cl2/hexane (5:45:50) to give 0.113 g of (S)-(+)-2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]acetonitrile.

Workup

  1. stirringthe mixture is stirred overnight
  2. temperaturethe temperature is increased to 90° C
  3. temperatureThe mixture is heated at that temperature for 5.5 h
  4. temperatureto cool
  5. stirringstir overnight
  6. customafter which the mixture is partitioned between ethyl acetate, aq. ammonium chloride, and brine
  7. dry with materialThe organic layers are dried over magnesium sulfate
  8. concentrationconcentrated
  9. customthe residue is chromatographed on silica gel gel (40 mL)
  10. washto elute unreacted

Sources & evidence

ORD record
ord-66cea0aab35a4ac4a2955f8201e4b7fc
Source dataset
uspto-grants-2002_09
Patent number
US06448397B1

Reaction notes

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