Diethyl Sulfate → HCID 54386540, compound

HRID 1067908Notes

Reaction equation

HRID 1067908 reaction equation
[C:1]([NH:5][CH:6]([CH3:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2].S(OCC)(O[CH2:13][CH3:14])(=O)=O.[OH-].[K+]>>[C:1]([N:5]([CH:6]([CH3:8])[CH3:7])[CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6163Diethyl SulfateHCID 14797Potassium HydroxideHCID 820232-Propanamine, 2-methyl-N-(1-methylethyl)-

Product 1

HCID 54386540HCID 54386540, compound

Procedure

A mixture of tert-butylisopropylamine (11.5 g, 0.1 mol) and diethyl sulfate (15.42 g, 0.1 mol) was refluxed for 2 h. Aqueous 8 M potassium hydroxide (20 ml, 0.16 mol) was added and the organic layer was separated. The aqueous layer was extracted with n-pentane (20 ml). The organic solutions were combined, dried over magnesium sulfate, and the product was isolated by distillation: 7.16 g, (50%), bp 140-142° C.; 1H NMR (CDCl3) δ0.99 (m, J=6.2 Hz, 9H, CH3), 1.10 (s, 9H, CH3), 2.55 (q, J=6.2 Hz, 2H, CH2, 3.35 (septet, J=6.2, 1H, CH).

Workup

  1. temperaturewas refluxed for 2 h
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with n-pentane (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. customthe product was isolated by distillation

Sources & evidence

ORD record
ord-82c4a6c43c574762b3226d2dad9a00f4
Source dataset
uspto-grants-2001_06
Patent number
US06248885B1

Reaction notes

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