Triethylamine → HCID 23282954, compound

HRID 370274Notes

Reaction equation

HRID 370274 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(Cl)(O[C:26](=[O:32])OC(Cl)(Cl)Cl)Cl.Cl.Cl.[NH2:36][CH:37]1[CH2:42][CH2:41][N:40]([CH2:43][CH:44]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]2)[CH2:39][CH2:38]1>O1CCCC1.O>[CH:44]1([CH2:43][N:40]2[CH2:41][CH2:42][CH:37]([NH:36][C:26]([C:11]3[CH:10]=[CH:9][CH:8]=[C:7]4[C:12]=3[NH:13][C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[O:6]4)=[O:32])[CH2:38][CH2:39]2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 67278PhenoxazineHCID 94429TriphosgeneHCID 23283031HCID 23283031, compound

Product 1

HCID 23282954HCID 23282954, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

50.3 mg of phenoxazine was dissolved in 3 ml of tetrahydrofuran at room temperature, and 0.15 ml of triethylamine and 86 mg of triphosgene were successively added thereto. After refluxed under heating for 30 minutes, 110 mg of 4-amino-1-cyclooctylmethylpiperidine dihydrochloride and 0.15 ml of triethylamine were added thereto, followed by reflux under heating for 2 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the obtained residue was purified by preparative thin layer chromatography (Kieselgel™60F254, Art5744 produced by Merck Co.: chloroform/methanol=30/1), and 105 mg of the title compound as a yellow solid was obtained.

Workup

  1. temperatureAfter refluxed
  2. temperatureunder heating for 30 minutes
  3. temperatureby reflux
  4. temperatureunder heating for 2 hours
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe obtained residue was purified by preparative thin layer chromatography (Kieselgel™60F254, Art5744 produced by Merck Co.: chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-b842b64c86da41e09ce5a69d95132cc7
Source dataset
uspto-grants-2000_10
Patent number
US06140338

Reaction notes

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