Water → HCID 54445176, compound

HRID 328589Notes

Reaction equation

HRID 328589 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)[CH2:2]1.[NH2-].[Na+].ClC(S(O[CH2:33][C:34]([F:37])([F:36])[F:35])(=O)=O)(Cl)Cl.O>O1CCCC1>[F:35][C:34]([F:37])([F:36])[CH2:33][N:1]1[CH2:6][CH2:5][O:4][CH:3]([CH2:7][N:8]2[C:9]3[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=3[CH:11]=[CH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]2=3)[CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24533Sodium amideHCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 21442782HCID 21442782, compound

Product 1

HCID 54445176HCID 54445176, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 5-(2-morpholinylmethyl)-5H-dibenz[b,f]azepine (0.23 g) in tetrahydrofuran was added sodium amide (0.063 g). The resulting mixture was stirred at 40° C for 30 minutes. To the reaction mixture was added trifluoroethyl trichloromethylsulfonate (0.265 g) in tetrahydrofuran at room temperature. The resulting mixture was stirred at 50° C for 5 hours. After cooling, the reaction mixture was admixed with water and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous sodium sulfate and evaporated to afford 5-(4-trifluoroethyl-2-morpholinylmethyl)-5H-dibenz[b,f]azepine. M.P. 97°-98° C.

Workup

  1. stirringThe resulting mixture was stirred at 50° C for 5 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-210074c58c434f3290ccdbc2d087f3d6
Source dataset
uspto-grants-1977_04
Patent number
US04017621

Reaction notes

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