Sodium Hydroxide → alpha-(o-Fluorophenyl)-alpha-[2-(diisopropylamino)ethyl]-alpha-[2-(2-methyl-1-piperidinyl)ethyl]acetamide

HRID 1855968Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH2:20][CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])([CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH3:19])[C:9]#[N:10].[OH-:29].[Na+]>S(=O)(=O)(O)O.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH2:20][CH2:21][N:22]([CH:23]([CH3:25])[CH3:24])[CH:26]([CH3:28])[CH3:27])([CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH3:19])[C:9]([NH2:10])=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

7 Parts of the preceding acetonitrile is dissolved in a solution of 67 parts by volume of concentrated sulfuric acid and 3 parts by volume of water. The resulting solution is heated on a steam bath for about 2 hours and then cooled to about 0° C. and made alkaline by the addition of diluted sodium hydroxide. The alkaline solution is extracted with ether, the ether extract dried over calcium sulfate, stripped of solvent and the residue crystallized from pentane to afford α-(o-fluorophenyl)-α-[2-(diisopropylamino)ethyl]-α-[2-(2-methyl-1-piperidinyl)ethyl]acetamide, melting at about 90°-91° C. This compound has the following structural formula ##STR30##

Workup

temperatureThe resulting solution is heated on a steam bath for about 2 hours
extractionThe alkaline solution is extracted with ether
extractionthe ether extract
dry with materialdried over calcium sulfate
customthe residue crystallized from pentane

Sources & evidence

ORD record: ord-ec22c3142b5143fbbd762507474f7ec1
Source dataset: uspto-grants-1980_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04217306

Reaction notes

Loading…