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

HRID 2198994
Notes
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Reaction equation

HRID 2198994 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23938PalladiumCatalyst
HCID 8028
Tetrahydrofuran
Solvent

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 1 M 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-f9a45d19bb9d403b997baed94dd53f08
Source dataset
uspto-grants-1982_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04360674

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes