Oxalyl chloride → 2-[2-(1-Piperidinyl)ethyl]pyridine

HRID 1086877Notes

Reaction equation

HRID 1086877 reaction equation
C(Cl)(=O)C(Cl)=O.NC[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:11][CH2:10]1>C(Cl)Cl.CN(C)C=O>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 151663604-(Aminomethyl)-1-(2-pyridylethyl)piperidine

Product 1

HCID 795482-[2-(1-Piperidinyl)ethyl]pyridineYield 73.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of benzofurazan-5(or 6)-carboxylic acid (150 mg, 0.91 mmol) in methylene chloride (3.3 ml) was added dimethylformamide (1 drop) followed by dropwise addition of oxalyl chloride (89 μl, 1.0 mmol). The resulting solution was stirred at room temperature for 3 hours and then concentrated under reduced pressure. The brown oil was redissolved in methylene chloride (3.3 ml) and was added to a cooled (0° C.) solution of 4-(aminomethyl)-1-(2-pyridylethyl)piperidine (0.21 g, 0.95 mmol) in methylene chloride (1.6 ml). The reaction mixture was stirred at 0° C. for 11/2 hours. Solvent evaporation, flash chromatography (silica gel, chloroform-methanol-ammonium hydroxide, 95/5/1/2) and trituration with hexane-ethyl acetate gave 4-[N-benzofurazan-5(or 6)-carbonyl)aminomethyl]-1-(2-pyridylethyl)piperidine (133 mg, 40%); mp 149°-151° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe brown oil was redissolved in methylene chloride (3.3 ml)
  3. additionwas added to
  4. stirringThe reaction mixture was stirred at 0° C. for 11/2 hours
  5. customSolvent evaporation, flash chromatography (silica gel, chloroform-methanol-ammonium hydroxide, 95/5/1/2) and trituration with hexane-ethyl acetate

Sources & evidence

ORD record
ord-9b9cc65aca7541e698efca28af72a80e
Source dataset
uspto-grants-1991_07
Patent number
US05032604

Reaction notes

Loading…