Piperidine → HCID 86747749, compound

HRID 128566Notes

Reaction equation

HRID 128566 reaction equation
[S:1](/[CH:4]=[CH:5]\[C:6]([OH:8])=O)[C:2]#[N:3].C(N(CC)CC)C.ClC(OCC)=O.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[S:1](/[CH:4]=[CH:5]\[C:6]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:8])[C:2]#[N:3]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 53838152-Propenoic acid, 3-thiocyanato-

Product 1

HCID 86747749HCID 86747749, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent4×

Procedure

To a stirred suspension of compound 2 (3.06 g., 0.023 mole) in 60 ml of dry toluene, triethylamine (2.35 g., 0.023 mole) in 10 ml of dry toluene was added dropwise, keeping the temperature of the mixture at 0°-5° C. To the resulting solution was added dropwise, ethyl chloroformate (2.53 g., 0.023 mole) in 15 ml of dry toluene at 0°-5° C. After stirring the mixture for 15 minutes, piperidine (2.0 g., 0.023 mole) in 15 ml of dry toluene was added dropwise at 0°-5° C. The mixture was allowed to warm to room temperature, stirred for an additional 2 hours and filtered. The filtrate was washed with water, dried (MgSO4) and concentrated to give an oil which solidified, 2.6 g. The solid was recrystallized from ethanol: mp 88°-90° C.; IR (KBr) 2175, 1630 cm-1

Workup

  1. additionwas added dropwise
  2. customat 0°-5° C
  3. additionTo the resulting solution was added dropwise
  4. customat 0°-5° C
  5. stirringstirred for an additional 2 hours
  6. filtrationfiltered
  7. washThe filtrate was washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customto give an oil which
  11. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-ffd5ec8a63004ca0af41101db072720c
Source dataset
uspto-grants-1995_11
Patent number
US05464832

Reaction notes

Loading…