Ethyl chloroformate → HCID 21474143, compound

HRID 2294072Notes

Reaction equation

HRID 2294072 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([C:16]3[CH2:21][CH2:20][N:19](C)[CH2:18][CH:17]=3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:23]=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].[NH4+].[OH-]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([C:16]3[CH2:21][CH2:20][NH:19][CH:18]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:17]=3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 214741298-Chloro-11-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Product 1

HCID 21474143HCID 21474143, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Dissolved 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-N-methyl-1,2,5,6-tetrahydropyridine (1.24 g, 3.82 mmol) in 100 mL of dry toluene, and added ethyl chloroformate (0.91 mL, 9.54 mmol) via syringe. Heated at 80° C. for 46 hours under a nitrogen atmosphere. Cooled to room temperature, and added 1N NH4OH. Extracted with ether. Purified crude product by flash chromatography on silica gel eluting with 10% EtOAc-CH2Cl2. Combined appropriate fractions, and evaporated to give 0.39 g (27% yield) of ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-1,2,5,6- tetrahydropyridinecarboxylate as an oil. mass spectrum: (Cl, CH4) m/e 383 (M+1) ##STR48##

Workup

  1. temperatureCooled to room temperature
  2. extractionExtracted with ether
  3. customPurified crude product by flash chromatography on silica gel eluting with 10% EtOAc-CH2Cl2
  4. customevaporated

Sources & evidence

ORD record
ord-5d41bcfbe1ae4645b2a2517bfce2d0d9
Source dataset
uspto-grants-1997_11
Patent number
US05688805

Reaction notes

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