3,3-Dimethylbutylamine → HCID 58168487, compound

HRID 909880Notes

Reaction equation

HRID 909880 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][NH2:5].[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH:11]=O>CO.[Pd].O>[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH2:11][NH:5][CH2:4][CH2:3][C:2]([CH3:7])([CH3:6])[CH3:1]

Participants

6

Reactant 2

HCID 197093,3-DimethylbutylamineHCID 162650Acetaldehyde, 2,2-dimethoxy-

Product 1

HCID 58168487HCID 58168487, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3,3-dimethylbutan-1-amine (1.33 mL) and 2,2-dimethoxyacetaldehyde (1.5 mL) in MeOH (10 mL) was added to palladium on carbon (0.316 g) in water (0.5 mL) at 25° C. The mixture of was hydrogenated under 5 bar at 25° C. for 3 h. The reaction mixture was filtered and concentrated in vacuo to afford N-(2,2-dimethoxyethyl)-3,3-dimethylbutan-1-amine (1.85 g) as a liquid. 1H NMR (300 MHz, CDCl3) δ 4.47 (t, J=5.6 Hz, 1H), 3.40 (s, 6H), 2.75 (d, J=5.8 Hz, 2H), 2.65-2.57 (m, 2H), 1.45-1.35 (m, 2H), 0.90 (s, 9H)

Workup

  1. additionThe mixture
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-607118ab1bc849a2a9ccf8cb1fc1d276
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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