Sodium Hydroxide → HCID 18612482, compound

HRID 1016370Notes

Reaction equation

HRID 1016370 reaction equation
[C:1]1([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>FC(F)(F)S(O)(=O)=O>[NH:18]1[CH2:19][CH2:20][CH:15]([CH:13]2[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH2:7][N:8]3[CH:12]=[CH:11][N:10]=[C:9]23)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18612505HCID 18612505, compound

Product 1

HCID 18612482HCID 18612482, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of α-[1-(phenylmethyl)-1H-imidazol-2-yl]-4-piperidinemethanol (5.4 g) in trifluoromethanesulfonic acid (25 ml) was stirred overnight at 100° C. The reaction mixture was cooled, poured out onto ice, then alkalized with NaOH and this mixture was extracted with DCM. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/(CH3OH/NH3) 95/5, upgrading to 90/10). The pure fractions were collected and the solvent was evaporated, yielding 2.5 g (50%) of 5,10-dihydro-10-(4-piperidinyl)-imidazo[1,2-b]isoquinoline (intermediate 10).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured out onto ice
  3. extractionthis mixture was extracted with DCM
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified over silica gel on a glass
  8. filtrationfilter (eluent: CH2Cl2/(CH3OH/NH3) 95/5, upgrading to 90/10)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f7246144a694423c906202fdaec09307
Source dataset
uspto-grants-2002_11
Patent number
US06476018B1

Reaction notes

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