1-Chloroethyl chloroformate → HCID 14850201, compound

HRID 2073178Notes

Reaction equation

HRID 2073178 reaction equation
ClC(OC(Cl)C)=O.[N:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH:22]1[CH2:27][CH2:26][N:25](CC2C=CC=CC=2)[CH2:24][CH2:23]1)[C:15]([C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)=[O:16]>ClCCCl>[N:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:15]([C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)=[O:16]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 14850200HCID 14850200, compound

Product 1

HCID 14850201HCID 14850201, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 1-chloroethyl chloroformate (9.7ml, 90 mmol) in 1,2-dichloroethane (25ml) was added to an ice-chilled solution of N-(2-pyrazinyl)-N-(1-phenylmethyl-4-piperidinyl)-2-furanamide (45 mmol) and 1,2-dichloroethane (125ml). The reaction mixture was stirred under reflux for 5 hours, then cooled and concentrated under vacuum. The crude carbamate residue was dissolved in methanol (150ml) and the reaction solution was heated under reflux for 2 hours. The reaction solution was cooled, decolorizing carbon (10g, Darco G-60) was added to the mixture, then the suspension was heated and stirred under reflux for 15 minutes. The suspension was filtered through Celite and the filtrate was concentrated under vacuum. The residue was suspended in hot isopropanol (100ml), then cooled and filtered. The pale maize colored powder was dried under vacuum (85° C., 0.01mm Hg, 2 hours) to yield N-(2-pyrazinyl)-N-(4piperidinyl)-2-furanamide (8.9g, 72%) as the hydrochloride salt.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperaturecooled
  3. concentrationconcentrated under vacuum
  4. dissolutionThe crude carbamate residue was dissolved in methanol (150ml)
  5. temperaturethe reaction solution was heated
  6. temperatureunder reflux for 2 hours
  7. temperatureThe reaction solution was cooled
  8. additionwas added to the mixture
  9. temperaturethe suspension was heated
  10. stirringstirred
  11. temperatureunder reflux for 15 minutes
  12. filtrationThe suspension was filtered through Celite
  13. concentrationthe filtrate was concentrated under vacuum
  14. temperaturecooled
  15. filtrationfiltered
  16. customwas dried under vacuum (85° C., 0.01mm Hg, 2 hours)

Sources & evidence

ORD record
ord-22a05c2ebee44308853d3486e16b6c30
Source dataset
uspto-grants-1990_04
Patent number
US04916142

Reaction notes

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