Trifluoroacetic acid → HCID 9909673, compound

HRID 585453Notes

Reaction equation

HRID 585453 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][N:26]6[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]6)=[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.FC(F)(F)C(O)=O>C(Cl)Cl>[N:26]1([CH2:25][CH2:24][O:23][C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:15]=2[C:14]2[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]34)[CH:11]=[CH:12][CH:13]=2)[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9849326HCID 9849326, compound

Product 1

HCID 9909673HCID 9909673, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 4-{2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]ethyl}-1-piperazinecarboxylate (0.406 g, 0.79 mmol) in CH2Cl2 (2 mL) is added trifluoroacetic acid (2 mL). The mixture is stirred at room temperature for 1 h then partitioned between CH2Cl2 and water. The organic layer is washed with saturated potassium carbonate, dried over anhydrous sodium sulfate and concentrated. Column chromatography (50 mL silica) using CH3OH/CH2Cl2 (8/92) with 2 drops per 100 mL of NH4OH gave 0.133 g (35%) of 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl 2-(1-piperazinyl)ethyl ether; mp 72° C.

Workup

  1. customthen partitioned between CH2Cl2 and water
  2. washThe organic layer is washed with saturated potassium carbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a092ce37ae9a41f4991e949b8e85ecae
Source dataset
uspto-grants-2005_08
Patent number
US06932961B1

Reaction notes

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