Pyridine → 1-(2-THIOPHENEACETYL)-4-(8-CHLORO-5,6-DIHYDRO-11H-BENZO[5,6]CYCLOHEPTA[1,2-b]PYRIDIN-11-YLIDENE)PIPERIDINE

HRID 840267Notes

Reaction equation

HRID 840267 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C: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.N1C=CC=CC=1.[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH2:34][C:35](Cl)=[O:36]>C(Cl)Cl>[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH2:34][C:35]([N:19]1[CH2:18][CH2:17][C:16](=[C:15]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]3[CH:22]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=3)[CH2:21][CH2:20]1)=[O:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 124087DesloratadineHCID 1623622-Thiopheneacetyl chloride

Product 1

HCID 226219311-(2-THIOPHENEACETYL)-4-(8-CHLORO-5,6-DIHYDRO-11H-BENZO[5,6]CYCLOHEPTA[1,2-b]PYRIDIN-11-YLIDENE)PIPERIDINE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 gm (3.22 mmole) of 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene) piperidine and 0.29 mL of pyridine in 20 mL of dry CH2Cl2 at 0° C. and under an argon atmosphere was added dropwise 0.438 mL (3.55 mmol) of 2-thiopheneacetyl chloride. After 30 minutes the mixture was washed with 1.0 N aqueous NaOH and then brine. The organic portion was dried over Na2SO4, filtered and converted in vacuo to provide a residue which was purified via flash chromatography (3% MeOH in CH2Cl2) and treated with activated carbon to provide the title compound as a glass.

Workup

  1. washAfter 30 minutes the mixture was washed with 1.0 N aqueous NaOH
  2. dry with materialThe organic portion was dried over Na2SO4
  3. filtrationfiltered
  4. customto provide a residue which
  5. customwas purified via flash chromatography (3% MeOH in CH2Cl2)
  6. additiontreated with activated carbon

Sources & evidence

ORD record
ord-706cfd5fb05641d6b7f09348ab421cc6
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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