3,3-Dimethylbutylamine → HCID 57475711, compound

HRID 506855Notes

Reaction equation

HRID 506855 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.[CH3:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][NH2:13].[BH4-].[Na+]>CO>[CH3:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][NH:13][CH2:7][C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 197093,3-DimethylbutylamineHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 57475711HCID 57475711, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-methyl-2-imidazolecarboxaldehyde (4 g, 0.036 mol) and 3,3-dimethylbutylamine (4.9 mL, 0.036 mol) in MeOH (100 mL) was stirred at room temperature for 1 hour before NaBH4 (2.0 g, 0.053 mol) was added in portions. The resulting solution was stirred at room temperature for another hour before quenching with water. MeOH was removed under vacuum from the resulting mixture, and the residue purified by column chromatography (0-15% MeOH/EtOAc) to yield a light yellow liquid.

Workup

  1. additionwas added in portions
  2. custombefore quenching with water
  3. customMeOH was removed under vacuum from the resulting mixture
  4. customthe residue purified by column chromatography (0-15% MeOH/EtOAc)
  5. customto yield a light yellow liquid

Sources & evidence

ORD record
ord-1aa360b02a63403d9ae751bdc72f160a
Source dataset
uspto-grants-2010_08
Patent number
US07786116B2

Reaction notes

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