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Diethyl Ether → 6,11-DIHYDRO-11-(4-PIPERIDINYL)-5H-BENZO[5,6]CYCLOHEPTA[1,2-b]PYRIDINE

HRID 1421251
Notes
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Reaction equation

HRID 1421251 reaction equation
Cl[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.CCOCC.[O-]S([O-])(=O)=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1>[NH:19]1[CH2:18][CH2:17][CH:16]([CH: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]=[CH:2][CH:3]=[CH:4][C:5]2=3)[CH2:21][CH2:20]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24083Sulfuric acid magnesium salt (1:1)HCID 24436Sodium SulfateHCID 124087Desloratadine

Product 1

HCID 106840186,11-DIHYDRO-11-(4-PIPERIDINYL)-5H-BENZO[5,6]CYCLOHEPTA[1,2-b]PYRIDINE

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution 66.27 g (0.21 mole) of 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta(1,2-b]pyridin-11-ylidene)-piperidine (product from Preparative Example 1 Example, step G), in THF (1 L) was added LiAIH4 (24.32 g, 0.64 mole) and the reaction mixture was heated to reflux overnight. The reaction mixture was then cooled to room temperature and ~3 L of Et2O is added followed by dropwise addition of saturated Na2SO4 until a white gray precipitate forms. MgSO4 was then added to the separated organic layer and stirred for 30 minutes. All the volatiles were then removed and the resulting crude mixture was chromatographed on a silica gel column eluting with 10% MeOH saturated with NH4OH in CH2Cl2. The material obtained contained both the desired compound and the des-chloro compound. Separation on HPLC using reverse phase column and eluting with 40% MeOH-water afforded the desired compounds as white solids (Product A's mp=95.2-96.1° C., Product B's mp=145.1-145.7° C.).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customAll the volatiles were then removed
  4. customthe resulting crude mixture was chromatographed on a silica gel column
  5. washeluting with 10% MeOH saturated with NH4OH in CH2Cl2
  6. customThe material obtained

Sources & evidence

ORD record
ord-8eb7976e9b5e46e5aa7cc60cbda91a57
Source dataset
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06075025

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes