Triethylamine → HCID 22288615, compound

HRID 968268Notes

Reaction equation

HRID 968268 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[O:25][C:26](=O)[CH2:27][CH2:28][C:29](Cl)=[O:30].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:29](=[O:30])[CH2:28][CH2:27][C:26]([NH:34][NH2:35])=[O:25])[CH2:10][CH2:11]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 109781561-[(3,4-Dichlorophenyl)methyl]piperidin-4-amine

Product 1

HCID 22288615HCID 22288615, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3,4-dichlorobenzyl)-piperidin-4-ylamine (2.2 g; JP 59101483) and triethylamine (1.53 ml) in dichloromethane (100 ml) stirring at ambient temperature was treated with 3-chlorocarbonyl-propionic acid methyl ester (1.14 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 2 hours and then allowed to cool. Water (30 ml) was added to the reaction mixture and the ethanol was evaporated. The aqueous residue was then extracted into dichloromethane (6×50 ml), the combined organics were dried (MgSO4) and evaporated to give the subtitle compound as a white solid. (1.9 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 2 hours
  7. temperatureto cool
  8. customthe ethanol was evaporated
  9. extractionThe aqueous residue was then extracted into dichloromethane (6×50 ml)
  10. dry with materialthe combined organics were dried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-96072b447e6141c69ff9ebd4987a9b0c
Source dataset
uspto-grants-2005_10
Patent number
US06958350B2

Reaction notes

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