Sodium Hydroxide → alpha,alpha-Bis[2-(diisopropylamino)ethyl]-alpha-phenylacetamide

HRID 262313Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2 Parts of α,α-bis[2-(diisopropylamino)ethyl]-α-phenylacetonitrile is dissolved in 20 parts by volume of concentrated sulfuric acid and the resulting solution heated on a steam bath for about 90 minutes. The solution is then cooled to about 0° C. and made alkaline by the addition of dilute sodium hydroxide. The alkaline solution is extracted with ether, the ether extract dried over calcium sulfate and stripped of solvent to afford α,α-bis[2-(diisopropylamino)ethyl]-α-phenylacetamide, melting at about 102°-103° C. after crystallization from hexane. This compound has the following structural formula ##STR14## cl EXAMPLE 4

Workup

temperaturethe resulting solution heated on a steam bath for about 90 minutes
extractionThe alkaline solution is extracted with ether
extractionthe ether extract
dry with materialdried over calcium sulfate

Sources & evidence

ORD record: ord-1dd64a36128744db8dc63df25265d159
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04153797

Reaction notes

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