N,N-Diisopropylethylamine

Description

N, N-Diisopropylethylamine (DIEA) is a base widely used in organic synthesis. The three relatively bulky alkyl groups attached to the nitrogen make DIEA a non-nucleophilic base.

Chemical properties

Diisopropylethylamine (DIPEA) is a clear, colorless to light yellow liquid, insoluble in water and easily soluble in acetone and other organic solvents.

The Uses of N,N-Diisopropylethylamine

N,N-Diisopropylethylamine is used as a base in organic reactions. Used in the preparation of (-)Gambierol a marine polycyclic ether toxin. It is also used in the synthesis of potent inhibitors of human brain memapsin, a key effector in the progression of Alzheimer’s disease.

What are the applications of Application

N,N-Diisopropylethylamine is an important pesticide and pharmaceutical intermediate, which can be used to synthesize anesthetics and herbicides, and can also be used as a sterically hindered amine to participate in various catalytic reactions.

Preparation

N,N-Diisopropylethylamine is used as a non-nucleophilic base in organic synthesis. It is prepared by the alkylation of diisopropylamine with diethyl sulphate. DIPEA can then be purified through distillation from potassium hydroxide if necessary.

Definition

ChEBI: N,N-Diisopropylethylamine (DIPEA) is a tertiary amino compound.

General Description

N-Ethyldiisopropylamine (EDIA) reacts with monoactivated Michael acceptors to afford symmetrical sulfones.

Flammability and Explosibility

Highly flammable

Synthesis

The synthesis method comprises the following steps (1) reacting paraldehyde serving as a raw material in a solvent under normal pressure and at the temperature of 22-28 ℃ under the action of an acidic catalyst for 20-40 minutes; (2) adding diisopropylamine and metal hydride serving as a reducing agent into a reaction product obtained by the step (1), preserving heat and reacting for 10-30 minutes to obtain the N, N-diisopropylethylamine, wherein the molar ratio of the diisopropylamine to the paraldehyde is 1:0.34-0.4, the molar ratio of the diisopropylamine to the metal hydride is 1:1-1.2, and the mass ratio of the acidic catalyst to the diisopropylamine is 1-5 percent; and (3) after removing the solvent under reduced pressure from reaction solution obtained by the step (2), adjusting pH (Potential of Hydrogen) to be 13, and then separating and rectifying to obtain the N, N-diisopropylethylamine.

Purification Methods

Distil the amine from ninhydrin, then from KOH [Dryland & Sheppard, J Chem Soc, Faraday Trans 1 125 1986]. It is a strong base and should be stored in the absence of carbon dioxide. [Hünig & Kiessel Chem Ber 91 380, 387 1958, Wotiz et al. J Org Chem 24 1202 1959, Beilstein 4 IV 551.]