Water → HCID 13315029, compound

HRID 1863487Notes

Reaction equation

HRID 1863487 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([CH:7]=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][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]([CH:7]=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)[CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24533Sodium amideHCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 13308996HCID 13308996, compound

Product 1

HCID 13315029HCID 13315029, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 5-(morpholin-2-yl)methylidene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (0.69 g) in anhydrous tetrahydrofuran was added sodium amide (0.20 g) at room temperature, and the resulting mixture was heated under reflux for 1.5 hours. After cooling, 2,2,2-trifluoroethyl trichloromethylsulfonate (0.666 g) in anhydrous tetrahydrofuran was added to the mixture under ice-cooling, and then the mixture was heated under reflux for 11.5 hours. After cooling, water (0.2 g) was added thereto and inorganic materials were eliminated by filtration. The filtrate was evaporated and chromatographed to afford 5-[4-(2,2,2-trifluoroethyl)morpholin-2-yl]methylidene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as oily material. M.P., 174°-177° C. (hydrochloride).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. temperaturecooling
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 11.5 hours
  7. temperatureAfter cooling
  8. filtrationinorganic materials were eliminated by filtration
  9. customThe filtrate was evaporated
  10. customchromatographed

Sources & evidence

ORD record
ord-8be374b0d3984419af4fa7c098754321
Source dataset
uspto-grants-1979_09
Patent number
US04169146

Reaction notes

Loading…