Triethylamine → HCID 19814330, compound

HRID 466601Notes

Reaction equation

HRID 466601 reaction equation
[C:1]([C:4]1([OH:15])[CH2:9][CH2:8][N:7]([C:10]([O:12]CC)=O)[CH2:6][CH2:5]1)(=O)[CH3:2].[C:16]([N:20]=[C:21]=[O:22])([CH3:19])([CH3:18])[CH3:17].[CH2:23](N(CC)CC)[CH3:24]>C(Cl)(Cl)Cl>[C:16]([N:20]1[C:1](=[CH2:2])[C:4]2([CH2:5][CH2:6][N:7]([C:10]([CH2:23][CH3:24])=[O:12])[CH2:8][CH2:9]2)[O:15][C:21]1=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 19814297HCID 19814297, compound

Product 1

HCID 19814330HCID 19814330, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture containing 4.3 g of 4-acetyl-1-ethoxycarbonyl-4-hydroxypiperidine, 6.0 g of tert-butyl isocyanate and 1 ml of triethylamine is refluxed under nitrogen for 6 hours. After cooling down and adding 50 ml of chloroform to the reaction mixture the organic phase is washed with water to neutral, then the solvent is evaporated under reduced pressure. The crude product obtained as evaporation residue is recrystallized from isopropyl ether to give the title substance in 44% yield, m.p.: 104°-105° C.

Workup

  1. temperatureis refluxed under nitrogen for 6 hours
  2. temperatureAfter cooling down
  3. washis washed with water to neutral, then the solvent
  4. customis evaporated under reduced pressure

Sources & evidence

ORD record
ord-87a9bdb8cc4843619ff3c8e10a113672
Source dataset
uspto-grants-1992_10
Patent number
US05157038

Reaction notes

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