Ethanol → α,α-Bis[2-[bis(1-methylethyl)amino]ethyl]-4-methylbenzeneacetamide

HRID 262315Notes

Reaction equation

HRID 262315 reaction equation
[CH:1]([N:4]([CH:26]([CH3:28])[CH3:27])[CH2:5][CH2:6][C:7]([CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[C:8]#[N:9])([CH3:3])[CH3:2].[OH-].[K+].C([OH:33])C>O>[CH:23]([N:19]([CH:20]([CH3:22])[CH3:21])[CH2:18][CH2:17][C:7]([CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH:26]([CH3:28])[CH3:27])([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[C:8]([NH2:9])=[O:33])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 12612220HCID 12612220, compound

Product 1

HCID 12612254α,α-Bis[2-[bis(1-methylethyl)amino]ethyl]-4-methylbenzeneacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 10 parts of the preceding acetonitrile, 20 parts of potassium hydroxide, 2 parts by volume of water and 50 parts by volume of ethanol is refluxed for 22 hours. The mixture is then cooled to room temperature, poured into water and extracted with ether. The ether extract is dried over calcium sulfate and stripped of solvent to afford an oil which solidifies upon standing. The crude solid is crystallized from pentane to afford α,α-bis[2-(diisopropylamino)ethyl]-α-(p-tolyl)acetamide, melting at about 97°-100° C. This compound is represented by the following structural formula ##STR17##

Workup

  1. temperatureis refluxed for 22 hours
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. dry with materialis dried over calcium sulfate
  5. customto afford an oil which
  6. customThe crude solid is crystallized from pentane

Sources & evidence

ORD record
ord-645f89f143a94ffb8dfcd94563d947c2
Source dataset
uspto-grants-1979_05
Patent number
US04153797

Reaction notes

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