Triethylamine → HCID 22914784, compound

HRID 1534582Notes

Reaction equation

HRID 1534582 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19](C)[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH:8]=[CH:7][C:6]=2[CH:23]=1.C(N(CC)CC)C.Cl[C:32]([O:34][CH2:35][C:36]([Cl:39])([Cl:38])[Cl:37])=[O:33].ClC([O-])=O>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:17][CH2:18][N:19]([C:32]([O:34][CH2:35][C:36]([Cl:39])([Cl:38])[Cl:37])=[O:33])[CH2:20][CH2:21]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH:8]=[CH:7][C:6]=2[CH:23]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 870632,2,2-Trichloroethyl chloroformateHCID 21226386CarbonochloridateHCID 229147868-Chloro-11-(1-methylpiperidin-4-ylidene)-11H-benzo[5,6]cyclohepta[1,2-b]pyridine

Product 1

HCID 22914784HCID 22914784, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 755 mg (2.34 mmole) of 8-chloro-11-(1-methyl-4-piperidylidene)-11H-benzo[5,6]cyclohepta[1,2-b]pyridine and 1.5 mL of triethylamine in 25 mL of dry toluene at room temperature and under a nitrogen atmosphere was added 650 μL (4.72 mmole) of 2,2,2-trichloroethyl chloroformate. The mixture was then heated to 90° C. Additional amounts of the chloroformate (500 μL and 300 μL) and triethylamine (1.0 mL each time) were added to the mixture after 2 hr. and 3 hr. 40 min., respectively. After a total reaction time of 5 hr. the mixture was poured into water and extracted three times with CH2Cl2. The combined organic portions were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography [11/2% MeOH in CH2Cl2 ] to afford 639 mg (56%) of the title compound as a glass.

Workup

  1. custom3 hr
  2. custom40 min.
  3. customAfter a total reaction time of 5 hr
  4. extractionextracted three times with CH2Cl2
  5. dry with materialThe combined organic portions were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via flash chromatography [11/2% MeOH in CH2Cl2 ]

Sources & evidence

ORD record
ord-b4c1e48b16954883bc8f6116d956a546
Source dataset
uspto-grants-1992_02
Patent number
US05089496

Reaction notes

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