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

HRID 2419609Notes

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 ##STR13##

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-02c8cdbd48cc48c288390aefb00e3f8c
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04107205

Reaction notes

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