Triethylamine → HCID 18357154, compound

HRID 427465Notes

Reaction equation

HRID 427465 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:7][CH:8]=1)#[N:2].Cl.Cl[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>O.C(O)(C)C>[N:21]1[CH:22]=[CH:23][C:18]([N:13]2[CH2:14][CH2:15][CH:10]([O:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[CH2:11][CH2:12]2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 18357113HCID 18357113, compound

Product 1

HCID 18357154HCID 18357154, compoundYield 10.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

4-(5-Cyano,2-pyridinoxy)piperidine (337 mg) and 4-chloropyridine hydrochloride (284 mg) were dissolved in water (10 mL) and treated with triethylamine (0.47 mL) in isopropanol (1 mL) and refluxed for 24 hours. The reaction was quenched by evaporation of the solvent. The residue was dissolved in dichloromethane and washed with aqueous sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated. The residue was triturated with diethyl ether to give 1-(4-pyridyl),4-(5-cyano,2-pyridinyloxy)piperidine (50 mg) as a pale cream crystalline solid; microanalysis, found: C, 66.4; H, 5.6; N, 19.0%; C16H16N3O0.5.H2O requires: C, 66.4; H, 5.9; N, 19.4%; NMR: (CDCl3) 1.90 (m,2H), 2.10 (m,2H), 3.32 (m,2H), 3.67 (m,2H), 5.37 (m,1H), 6.68 (d,2H), 6.80 (d,1H), 7.78 (dd,1H), 8.28 (d,2H), 8.47 (d,1H): MS: m/z 281 (MH)+.

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe reaction was quenched by evaporation of the solvent
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with aqueous sodium hydrogen carbonate solution, water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-e1a5a677ff1a4c769490d2dce6da6832
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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