3,3-Dimethylbutylamine → HCID 178444760, compound

HRID 1695954Notes

Reaction equation

HRID 1695954 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)=O.[CH3:22][C:23]([CH3:28])([CH3:27])[CH2:24][CH2:25][NH2:26]>C1(C)C=CC=CC=1>[CH3:22][C:23]([CH3:28])([CH3:27])[CH2:24][CH2:25]/[N:26]=[CH:1]/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 197093,3-DimethylbutylamineHCID 57774373HCID 57774373, compound

Product 1

HCID 178444760HCID 178444760, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 4-(2-formylphenyl)piperidine-1-carboxylate (229 mg, 0.79 mmol) in toluene (4 mL) was added 3,3 dimethylbutylamine (88.09 mg, 117.1 μL, 0.8705 mmol) and 4 Å molecular sieves. The resulting suspension was stirred at rt overnight. Filtered out molecular sieves and concentrated the mixture with a flow of N2 to give 282 mg of tert-butyl 4-(2-((E)-(3,3-dimethylbutylimino)methyl)phenyl)piperidine-1-carboxylate as an thick off-white oil which was used without further purification for the next step.

Workup

  1. filtrationFiltered out molecular sieves
  2. concentrationconcentrated the mixture with a flow of N2

Sources & evidence

ORD record
ord-0dcc8210f3d64d3d80ddc3d79a735df4
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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