Acetic Acid → HCID 54135013, compound

HRID 1292578Notes

Reaction equation

HRID 1292578 reaction equation
C([Li])CCC.[CH2:6]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:19](OCC)(=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(O)(=O)C>COC(C)(C)C.C1(C)C=CC=CC=1.O>[CH2:23]([O:22][C:20](=[O:21])[C:19]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:25])[CH3:24]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 761901-BenzylpiperidineHCID 178418339Butyllithium

Product 1

HCID 54135013HCID 54135013, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of n-butyllithium in toluene (20%; 65.6 g; 0.20 mol) is added over the course of from 10 to 15 min to a solution of 31 g of N-benzylpiperidine (0.175 mol) in 60 ml of tert-butyl methyl ether. The reaction mixture is heated at from 55° to 60° C. for approximately 18 h and then metered at RT into a cold (-20° C.) solution of 50.1 g of diethyl oxalate (0.42 mol) in 160 ml of toluene. The mixture is heated to RT and stirred at from 20° to 25° C. for 30 min. Acetic acid (100%; 12.6 g; 0.21 mol) and a mixture of 50 g of crushed ice and 100 g of water are then added to the reaction mixture. The phases are separated and the organic phase is washed with 50 ml of water and concentrated by evaporation in vacuo: 43.2 g (content 89%; yield 80%).

Workup

  1. temperatureThe reaction mixture is heated at from 55° to 60° C. for approximately 18 h
  2. additionare then added to the reaction mixture
  3. customThe phases are separated
  4. washthe organic phase is washed with 50 ml of water
  5. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-e8803f2b00bc4e758b71eb2464a3944f
Source dataset
uspto-grants-1998_05
Patent number
US05756811

Reaction notes

Loading…