Piperidine → HCID 21442752, compound

HRID 328618Notes

Reaction equation

HRID 328618 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N+:8]([O-:18])[CH2:9][C:10]3[N:11]([N:12]=[C:13]([C:15]([OH:17])=O)[N:14]=3)[C:5]=2[S:4][C:3]=1[CH3:25].C(N(CC)CC)C.C(Cl)(=O)OCC.[NH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>O.O1CCCC1>[CH3:1][C:2]1[C:6]2[C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N+:8]([O-:18])[CH2:9][C:10]3[N:11]([N:12]=[C:13]([C:15]([N:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)=[O:17])[N:14]=3)[C:5]=2[S:4][C:3]=1[CH3:25]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 86734656HCID 86734656, compound

Product 1

HCID 21442752HCID 21442752, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 178 mg. of 7,8-dimethyl-6-phenyl-4H-thieno[3,2-f]-s-triazolo[1,5-a][1,4]diazepine-2-carboxylic acid 5-oxide, 0.1 ml. of triethylamine and 5 ml. of tetrahydrofuran is added 0.07 ml. of ethyl chlorocarbonate under stirring and cooling on an ice-sodium chloride bath, and the mixture is stirred for 5 minutes. Then, to the mixture is added 0.07 ml. of piperidine, followed by stirring for 30 minutes, and water is added to the resulting mixture. Then, the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried over sodium sulfate and then the solvent is evaporated. Thereafter, addition of ether to the residue gives 7,8-dimethyl-6-phenyl-2-piperidinocarbonyl-4H-thieno[3,2-f]-s-triazolo[1,5-a][1,4]diazepine-5-oxide as crystals. Recrystallization from ethyl acetate gives colorless prisms melting at 213° to 214° C.

Workup

  1. additionTo a mixture of 178 mg
  2. temperaturecooling on an ice-sodium chloride bath
  3. additionThen, to the mixture is added 0.07 ml
  4. stirringby stirring for 30 minutes
  5. extractionThen, the mixture is extracted with ethyl acetate
  6. washThe ethyl acetate layer is washed with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent is evaporated
  9. additionThereafter, addition of ether to the residue

Sources & evidence

ORD record
ord-c2263c1cd08241c0b009e45afdab2690
Source dataset
uspto-grants-1977_04
Patent number
US04017620

Reaction notes

Loading…