Triethylamine → 1-(4-methylphenyloxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime

HRID 484335

Reaction equation

HRID 484335 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([O:7][C:8](Cl)=[O:9])=[CH:3][CH:2]=1.[CH3:12][O:13][N:14]=[CH:15][C:16]1[CH2:17][NH:18][CH2:19][CH2:20][CH:21]=1.C(N(CC)CC)C>ClCCl>[CH3:12][O:13][N:14]=[CH:15][C:16]1[CH2:17][N:18]([C:8]([O:7][C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)=[O:9])[CH2:19][CH2:20][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70304p-Tolyl chloroformateHCID 197313HCID 197313, compound

Product 1

HCID 30728641-(4-methylphenyloxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloximeYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of p-tolylchloroformate (1.5 mL, 10.3 mmoles) in dichloromethane (15 mL) was added under nitrogen at 0° C. to a stirred solution of 1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-methyloxime (1.3 g, 9.3 mmoles) and triethylamine (1.3 mL, 2.3 mmoles) in dichloromethane (20 mL). The reaction mixture was stirred at room temperature for 20 minutes, the solvent was evaporated and the residue was partitioned between water and ethylacetate. The organic layer was dried (Na2SO4) and evaporated. The solid was triturated with cyclohexane to afford 2.3 g (91%) of a white solid with mp 70°-71° C.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between water and ethylacetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated
  5. customThe solid was triturated with cyclohexane

Sources & evidence

ORD record
ord-9de783cbaa2b4fa6addc4ca21f17934b
Source dataset
uspto-grants-1993_07
Patent number
US05231107

Linked notes

Loading…