Piperidine → HCID 18001072, compound

HRID 1249995Notes

Reaction equation

HRID 1249995 reaction equation
ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[O:13]([CH2:20]CO)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH2:23][C:24]1[CH:42]=[CH:41][C:27]([C:28]([N:30]2[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:29])=[C:26]([Cl:43])[CH:25]=1.N1CCCCC1>C(Cl)(Cl)Cl>[O:13]([CH2:20][CH2:7][O:6][C:5]([NH:23][C:24]1[CH:42]=[CH:41][C:27]([C:28]([N:30]2[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:29])=[C:26]([Cl:43])[CH:25]=1)=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 31236PhenoxyethanolHCID 94429TriphosgeneHCID 10828112HCID 10828112, compound

Product 1

HCID 18001072HCID 18001072, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To chloroform (5 ml) is added triphosgen (0.72 g), and thereto is added with stirring 2-phenoxyethanol (1.0 g) under ice-cooling, during which the temperature of the reaction solution is kept at below 10° C., and the mixture is stirred at 0° C. for one hour. To the reaction solution are added with stirring dropwise 1-(4-amino-2-chlorobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.9 g) and a solution of piperidine (2.5 g) in chloroform (30 ml) under ice-cooling. The mixture is stirred at room temperature for three hours, washed with a saturated aqueous potassium hydrogen sulfate solution, distilled water and a saturated aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate, filtered, and evaporated to remove the solvent. The residue is recrystallized from diethyl ether to give 1-[4-(2-phenoxyethoxycarbonylamino)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.3 g) as white powder.

Workup

  1. temperaturecooling, during which the temperature of the reaction solution
  2. customis kept at below 10° C.
  3. additionTo the reaction solution are added
  4. stirringThe mixture is stirred at room temperature for three hours
  5. washwashed with a saturated aqueous potassium hydrogen sulfate solution
  6. distillationdistilled water
  7. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto remove the solvent
  11. customThe residue is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-bd347d8dda924f03a4932636e989064d
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

Loading…