Sodium Hydroxide → 1-Methyl-2-[2-(4-phenyl-1-piperidinyl)ethyl]-1H-naphth[1,2-d]imidazole

HRID 1462895Notes

Reaction equation

HRID 1462895 reaction equation
Br[C:2]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:5]2[N:6]([CH3:24])[C:7]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:15]N(CC4C=CC=CC=4)[CH2:13][CH2:12]3)=[N:8][C:4]=2[CH:3]=1.[OH-].[Na+].[H][H]>[Pd].O1CCCC1>[CH3:24][N:6]1[C:5]2[C:25]3[C:30]([CH:2]=[CH:3][C:4]=2[N:8]=[C:7]1[CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH:26]([C:25]2[CH:30]=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH2:15][CH2:16]1)=[CH:29][CH:28]=[CH:27][CH:26]=3

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 140725035-Bromo-2-[2-(4-benzyl-1-piperazinyl)ethyl]-1-methyl-1H-naphth[1,2-d]imidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 140725111-Methyl-2-[2-(4-phenyl-1-piperidinyl)ethyl]-1H-naphth[1,2-d]imidazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8.32 g (0.0185 mole) of the compound of Example 16, 0.9 g of 10% Pd-C catalyst, and 150 cc of tetrahydrofuran containing 20 cc of 1M NaOH is shaken in a Paar hydrogenator under about 5.4 atm. of hydrogen pressure until hydrogenolysis is completed. The catalyst is filtered and the mother liquor is concentrated to remove the solvent. The residue is taken up with methylene chloride, and washed with water. Upon evaporating the solvent, 6.1 g of a crude product are obtained which is recrystallized from acetone yielding 4.74 g of the compound of the title. M.p. 181.5°-182.5° C.

Workup

  1. filtrationThe catalyst is filtered
  2. concentrationthe mother liquor is concentrated
  3. customto remove the solvent
  4. washwashed with water
  5. customUpon evaporating the solvent, 6.1 g of a crude product
  6. customare obtained which
  7. customis recrystallized from acetone yielding 4.74 g of the compound of the title

Sources & evidence

ORD record
ord-1d269308136a4d1b910ee32b77f1706a
Source dataset
uspto-grants-1984_07
Patent number
US04461894

Reaction notes

Loading…