4-(9,10-Dihydro-10-methyl-9-acridinyl)-1-(2,2,2-trichloroethyloxycarbonyl)piperidine → 9,10-Dihydro-10-methyl-9-(4-piperidinyl)acridine

HRID 36613Notes

Reaction equation

HRID 36613 reaction equation
[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([CH:16]2[CH2:21][CH2:20][N:19](C(OCC(Cl)(Cl)Cl)=O)[CH2:18][CH2:17]2)[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2>C(O)(=O)C.[Zn]>[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 1

HCID 152894794-(9,10-Dihydro-10-methyl-9-acridinyl)-1-(2,2,2-trichloroethyloxycarbonyl)piperidine

Product 1

HCID 152894809,10-Dihydro-10-methyl-9-(4-piperidinyl)acridine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

Zinc dust (1.3 g, 20 mmol) is added to a solution of the crude product from step A in 20 mL glacial acetic acid maintained at 85° C. The reaction mixture is filtered after 30 minutes and concentrated in vacuo. The residue is then diluted with water, basified with a 1.0N aqueous NaOH solution, and extracted with CH2Cl2. The extract is dried with Na2SO4, filtered and concentrated in vacuo. The residue is then purified via flash chromatography (MeOH/CH2Cl2) to provide the title compound.

Workup

  1. filtrationThe reaction mixture is filtered after 30 minutes
  2. concentrationconcentrated in vacuo
  3. additionThe residue is then diluted with water
  4. extractionextracted with CH2Cl2
  5. dry with materialThe extract is dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is then purified via flash chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b5cecb5335044841b71ce88453132533
Source dataset
uspto-grants-1995_05
Patent number
US05416087

Reaction notes

Loading…