Triethylamine → 8-Fluoro-11(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

HRID 542756Notes

Reaction equation

HRID 542756 reaction equation
[F: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[CH2:8][CH2:7][C:6]=2[CH:23]=1.C(N(CC)CC)C.[CH2:31]([O:33][C:34](Cl)=[O:35])[CH3:32]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:17][CH2:18][N:19]([C:34]([O:33][CH2:31][CH3:32])=[O:35])[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:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 13920595HCID 13920595, compound

Product 1

HCID 139205968-Fluoro-11(1-ethoxycarbonyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridineYield 81.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 8-fluoro-11-(1-methyl-4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (10.5 g, 34 mmol) and triethylamine (5.2 g, 52 mmol) in dry toluene (120 mL) at 80° C. under an argon atmosphere, was added ethylchloroformate (18.5 g, 170 mmol) via a syringe. The reaction mixture was allowed to stir at this temperature for 30 minutes and at room temperature for one hour. The reaction mixture was then filtered and solvent was removed. The residue was triturated with pentane to give 10.1 grams (yield=81%) of the title compound, m.p.=116°-118° C.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customsolvent was removed
  3. customThe residue was triturated with pentane

Sources & evidence

ORD record
ord-76754af54ece4b7a862d53b27e26178c
Source dataset
uspto-grants-1987_04
Patent number
US04659716

Reaction notes

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