Sodium Hydroxide → Ammonium Hydroxide

HRID 1773881Notes

Reaction equation

HRID 1773881 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([I:15])[N:12]=[C:11]1[CH:16]=[O:17].FC(F)(F)S(O)(=O)=O.[OH:26][CH:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1.[OH-].[Na+]>O>[NH4+:10].[OH-:17].[Cl:1][C:2]1[C:3]2[CH2:8][CH2:9][N:10]3[C:11](=[N:12][C:13]([I:15])=[CH:14]3)[CH:16]([O:26][CH:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 660484-Piperidinol, 1-methyl-HCID 86703962HCID 86703962, compound

Product 2

HCID 14923Ammonium HydroxideHCID 72694673HCID 72694673, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1-[2-(2-chlorophenyl)ethyl]-4-iodoimidazole-2-carbaldehyde (example 78B) (200 mg, 0.55 mmole) is added trifluoromethanesulfonic acid (2 mL). The purple solution is stirred at room temperature overnight, 4-hydroxy-N-methylpiperidine (190 mg, 1.65 mmole) is added and solution is stirred at room temperature for 2 hours. Water is added and the solution is made alkaline by adding 5N NaOH to pH 10. The aqueous phase is extracted with AcOEt. The organic phase is washed with water, brine, dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH) (100:0) to (90:10) then (CH2Cl2:MeOH:NH4OH) (9:1:0.1) to give 8-chloro-2-iodo-4-(1-methyl piperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene.

Workup

  1. stirringsolution is stirred at room temperature for 2 hours
  2. extractionThe aqueous phase is extracted with AcOEt
  3. washThe organic phase is washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with (CH2Cl2:MeOH) (100:0) to (90:10)

Sources & evidence

ORD record
ord-ccaf0255d34b4c6e82de14840d502f06
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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