Ethanol → HCID 69522441, compound

HRID 968771Notes

Reaction equation

HRID 968771 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH2:14])[CH2:8][CH2:7]1.C(N(CC)CC)C.[OH2:26].[NH2:27][NH2:28].[CH2:29]([OH:31])[CH3:30]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][NH:14][C:30](=[O:26])[C:29]([NH:27][NH2:28])=[O:31])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 113582094-(3,4-Dichlorophenoxy)-1-piperidineethanamine

Product 1

HCID 69522441HCID 69522441, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 3, Step b (0.85 g) and triethylamine (0.82 ml) at RT in dichloromethane (20 ml) was added methyl oxalyl chloride (0.30 ml) dropwise over 10 minutes. The reaction mixture was partitioned between water (20 ml) and dichloromethane (20 ml). The organic phase was separated and dried with MgSO4. Evaporation under reduced pressure gave an oil which was dissolved in ethanol (10 ml) at RT and treated with hydrazine hydrate (1 ml) The reaction mixture was stirred at reflux for 24 hours, filtered and the filtrate evaporated under reduced pressure to leave an oil. Purification by flash chromatography (dichloromethane:methanol 90:10)gave the sub-title compound as a white solid (0.18 g).

Workup

  1. customThe reaction mixture was partitioned between water (20 ml) and dichloromethane (20 ml)
  2. customThe organic phase was separated
  3. dry with materialdried with MgSO4
  4. customEvaporation under reduced pressure
  5. customgave an oil which
  6. temperatureat reflux for 24 hours
  7. filtrationfiltered
  8. customthe filtrate evaporated under reduced pressure
  9. customto leave an oil
  10. customPurification by flash chromatography (dichloromethane

Sources & evidence

ORD record
ord-3ddb5fc434d641dcb08a4eb1c88b3666
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

Loading…