Dimethylamine → HCID 9820830, compound

HRID 1279720Notes

Reaction equation

HRID 1279720 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]Cl)=[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.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:35][NH:36][CH3:37].C1COCC1>CN(C=O)C>[CH3:35][N:36]([CH3:37])[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

7

Reactant 5

HCID 674DimethylamineHCID 5238Sodium IodideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 121486367-(2-Chloroethoxy)-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazole

Product 1

HCID 9820830HCID 9820830, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-chloroethyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether (0.248 g, 0.68 mmol) in dry DMF (10 mL) is added potassium carbonate (0.376 g, 2.7 mmol), sodium iodide (0.101 g, 0.68 mmol), and 2M dimethylamine in THF (0.68 mL, 1.36 mmol). The mixture is stirred for 48 h at room temperature. The mixture is then partitioned between water and Et2O. The organic layer is washed three times with water (100 mL), dried over anhydrous sodium sulfate and concentrated. Column chromatography (50 mL silica) using CH2Cl2 followed by CH3OH/CH2Cl2 (95/5) as eluent and then drying of the appropriate fractions under house vacuum gave 0.020 g (8%) of N,N-dimethyl-2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine; mp 117-118°

Workup

  1. customThe mixture is then partitioned between water and Et2O
  2. washThe organic layer is washed three times with water (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customdrying of the appropriate fractions under house vacuum

Sources & evidence

ORD record
ord-a464982cbe5948f78c34ebe6c6f34a53
Source dataset
uspto-grants-2002_09
Patent number
US06448397B1

Reaction notes

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