Diisopropylamine → N,N-Diisopropylisobutylamine

HRID 374665Notes

Reaction equation

HRID 374665 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C1(S(O[CH2:18][CH:19]([CH3:21])[CH3:20])(=O)=O)C=CC=CC=1.[OH-].[K+]>>[CH:1]([N:4]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 7912DiisopropylamineHCID 14797Potassium HydroxideHCID 63651822-Methylpropyl benzenesulfonate

Product 1

HCID 3312177N,N-DiisopropylisobutylamineYield 68%

Procedure

A mixture of diisopropylamine (20.24 g, 0.2 mol) and isobutyl phenylsulfonate (29.83 g, 0.1 mol) was refluxed with stirring for 72 hours. Aqueous 5M potassium hydroxide (30 ml, 0.15 mol) was added. The organic phase was separated and the aqueous phase was extracted with n-pentane (50 ml). The organic solutions were combined, dried over anhydrous magnesium sulfate and the produce was isolated by distillation to yield 10.70 g, 68% of the title product, bp 75-77° C./45 mm Hg. 1H NMR CDCl3 δ ppm, 0.83 (d, J=6.5 Hz, 6H, CH3), 0.95 (d, J=6.5 Hz, 12H, CH3), 1.59 (nonet, J=6.5 Hz, 1H, CH), 2.10 (d, J=6.5 Hz, 2H, CH2), 2.95 (sep, J=6.5 Hz, 2H, CH).

Workup

  1. temperaturewas refluxed
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with n-pentane (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe produce was isolated by distillation

Sources & evidence

ORD record
ord-250dcf179c184b80add4b7abb2c2d348
Source dataset
uspto-grants-1996_01
Patent number
US05481038

Reaction notes

Loading…