Sodium Hydroxide → 4-(2-ethyl-1-(1H-imidazol-1-yl)butyl)aniline

HRID 1894769Notes

Reaction equation

HRID 1894769 reaction equation
[CH2:1]([CH:3]([CH2:20][CH3:21])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([NH:16]C(=O)C)=[CH:12][CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)[CH3:2].[OH-].[Na+]>Cl>[CH2:20]([CH:3]([CH2:1][CH3:2])[CH:4]([C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86681896N-(4-(2-ethyl-1-(1H-imidazol-1-yl)butyl)phenyl)acetamide

Product 1

HCID 866818974-(2-ethyl-1-(1H-imidazol-1-yl)butyl)aniline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(4-(2-ethyl-1-(1H-imidazol-1-yl)butyl)phenyl)acetamide (350 mg, 1.23 mmol) in 3N HCl (3.28 mL) was stirred overnight at 60° C. After cooling to room temperature, the solution was poured onto ice and basified with 6N NaOH (pH=12-14). The aqueous phase was extracted three times with DCM and the organic extracts were combined and dried over MgSO4, filtered and then concentrated to afford to 4(2-ethyl-1-(1H-imidazol-1-yl)butyl)aniline. MS (ES+): m/z 244.31 (MH+).

Workup

  1. additionthe solution was poured onto ice
  2. extractionThe aqueous phase was extracted three times with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-70583211e1614cd4bf56ff28e0c07f0d
Source dataset
uspto-grants-2013_08
Patent number
US08513291B2

Reaction notes

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