Ethyl chloroformate → HCID 10715089, compound

HRID 1940669Notes

Reaction equation

HRID 1940669 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([CH:16]3[CH2:17][CH2:18][N:19]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:21]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 10495356HCID 10495356, compound

Product 1

HCID 10715089HCID 10715089, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8-Chloro-6,11-dihydro-11-(4-piperidinyl)-5H-benzo[5,6]cyclohepta-[1,2-b]pyridine (product from Example 233A) (4.18 g, 13 mmol) was dissolved in toluene (175mL). Ethyl chloroformate(11.6 g, 110 mmol, 10.2 mL) was then added and the reaction mixture was heated to ~120° C. overnight. All volatiles were stripped off and the crude product was purified on silica gel column eluting with 50% EtOAc- hexanes to give the title compound as a white solid(MH+ 385).

Workup

  1. temperaturethe reaction mixture was heated to ~120° C. overnight
  2. customthe crude product was purified on silica gel column
  3. washeluting with 50% EtOAc- hexanes

Sources & evidence

ORD record
ord-8de4ff939a64421f812209ac7667687d
Source dataset
uspto-grants-1997_12
Patent number
US05700806

Reaction notes

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