Triethylamine → HCID 22288616, compound

HRID 968272Notes

Reaction equation

HRID 968272 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH2:12])[CH2:8][CH2:7]1.C(N(CC)CC)C.C([CH:26]([C:30](Cl)=[O:31])[C:27](Cl)=[O:28])C.O.[NH2:34][NH2:35]>ClCCl.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([NH:12][C:27](=[O:28])[CH2:26][C:30]([NH:34][NH2:35])=[O:31])[CH2:10][CH2:11]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 109209242-Ethylpropanedioyl dichlorideHCID 109781561-[(3,4-Dichlorophenyl)methyl]piperidin-4-amine

Product 1

HCID 22288616HCID 22288616, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3,4-dichlorobenzyl)-piperidin-4-ylamine (2.5 g) and triethylamine (1.50 ml) in dichloromethane (100 ml) stirring at ambient temperature was treated with ethylmalonyl chloride (1.35 ml). After stirring for 16 hours, the reaction mixture was washed with brine, the organic layer was dried (MgSO4), and evaporated to leave a white solid. This solid was suspended in ethanol (100 ml), treated with hydrazine hydrate (5 ml) and the resulting mixture was stirred at reflux for 16 hours and then allowed to cool. Water (100 ml) was added to the reaction mixture and the ethanol was evaporated. The residue was then extracted with dichloromethane (3×100 ml), the combined organics were dried (MgSO4), evaporated. The resultant solid was triturated with diethyl ether to give the subtitle compound as a white solid. (2.27 g)

Workup

  1. washthe reaction mixture was washed with brine
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto leave a white solid
  5. stirringthe resulting mixture was stirred
  6. temperatureat reflux for 16 hours
  7. temperatureto cool
  8. customthe ethanol was evaporated
  9. extractionThe residue was then extracted with dichloromethane (3×100 ml)
  10. dry with materialthe combined organics were dried (MgSO4)
  11. customevaporated
  12. customThe resultant solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-71669d1419c841128a3e6bae8286288d
Source dataset
uspto-grants-2005_10
Patent number
US06958350B2

Reaction notes

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