Piperidine → HCID 15106964, compound

HRID 2108065Notes

Reaction equation

HRID 2108065 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][C:19]([OH:21])=O)[S:17][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[CH:10]([CH3:26])[N:9]=1.O[N:28]1[C:32]2C=[CH:34][CH:35]=[CH:36][C:31]=2N=N1.N1CCCCC1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][C:19]([N:28]3[CH2:34][CH2:35][CH2:36][CH2:31][CH2:32]3)=[O:21])[S:17][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[CH:10]([CH3:26])[N:9]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 15106956HCID 15106956, compound

Product 1

HCID 15106964HCID 15106964, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.1 g of 2-[4-(2-chlorophenyl)-6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]acetic acid in 15 ml of dimethylformamide are added 0.4 g of N-hydroxybenzotriazole and 0.3 g of piperidine and stirred at room temperature for 10 minutes. To the mixture is added 0.65 g of dicyclohexyl carbodiimide under ice-cooling and stirred for 1 hour and furthermore stirred at room temperature for 21 hours. The resulting dicyclohexylurea is filtered off and to the filtrate is added 100 ml of chloroform. The solution is washed with 5% aqueous sodium hydrogen-carbonate solution and water and dried over anhydrous magnesium sulfate. After separating by filtration, the filtrate is concentrated under reduced pressure and the residue is crystallized from isopropyl ether. The precipitated crystals are collected by filtration and recrystallized from ethyl acetate to give 0.9 g of 2-[4-(2-chlorophenyl)-6,9-dimethyl-6H-thieno[3,2-f][1,2,4 ]triazolo[4,3-a][1,4]diazepin-2-yl]acetic acid piperidide as colorless crystals, melting at 182°-183° C.

Workup

  1. temperaturecooling
  2. stirringstirred for 1 hour
  3. stirringfurthermore stirred at room temperature for 21 hours
  4. filtrationThe resulting dicyclohexylurea is filtered off and to the filtrate
  5. additionis added 100 ml of chloroform
  6. washThe solution is washed with 5% aqueous sodium hydrogen-carbonate solution and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter separating by filtration
  9. concentrationthe filtrate is concentrated under reduced pressure
  10. customthe residue is crystallized from isopropyl ether
  11. filtrationThe precipitated crystals are collected by filtration
  12. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f9ac2c6e7e524b04aa99cfc0d436de62
Source dataset
uspto-grants-1990_06
Patent number
US04937240

Reaction notes

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