3,3-Dimethylbutylamine → HCID 178444763, compound

HRID 1695958Notes

Reaction equation

HRID 1695958 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=O)[C:3]=1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.[CH3:23][C:24]([CH3:29])([CH3:28])[CH2:25][CH2:26][NH2:27]>C1(C)C=CC=CC=1>[CH3:23][C:24]([CH3:29])([CH3:28])[CH2:25][CH2:26]/[N:27]=[CH:8]/[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 197093,3-DimethylbutylamineHCID 57774387Tert-butyl 4-(2-fluoro-6-formylphenyl)piperidine-1-carboxylate

Product 1

HCID 178444763HCID 178444763, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 4-(2-fluoro-6-formylphenyl)piperidine-1-carboxylate (1.0 g, 4.23 mmol) in toluene (14 mL) was added 3,3 dimethylbutylamine (428.0 mg, 569.1 μL, 4.230 mmol) and 4 Å molecular sieves. The resulting solution was stirred at rt overnight. The molecular sieves were filtered off and the mixture concentrated in vacuo to give 1.5 g of tert-butyl 4-(2-((E)-(3,3-dimethylbutylimino)methyl)-6-fluorophenyl)piperidine-1-carboxylate as an off-white solid (1.5 g). The material was used without further purification for the next step. 1H-NMR in CD3CN of the crude was consistent for the product with a diagnostic peak of the imine proton @ 8.74 ppm.

Workup

  1. filtrationThe molecular sieves were filtered off
  2. concentrationthe mixture concentrated in vacuo

Sources & evidence

ORD record
ord-6d04d5448abe40ff8c809ca3ca0515ed
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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