Sulfuric acid magnesium salt (1:1) → 6,11-DIHYDRO-11-(4-PIPERIDINYL)-5H-BENZO[5,6]CYCLOHEPTA[1,2-b]PYRIDINE

HRID 2297643Notes

Reaction equation

HRID 2297643 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.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.CCOCC>[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

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24436Sodium SulfateHCID 124087DesloratadineHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

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 LiAlH4 (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-fa07e37c5f5a4fa6b895b2ec9c6f4584
Source dataset
uspto-grants-2002_12
Patent number
US06492381B1

Reaction notes

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