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

HRID 1855968
Notes
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Reaction equation

HRID 1855968 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12612248alpha-(o-Fluorophenyl)-alpha-[2-(diisopropylamino)ethyl]-alpha-[2-(2-methyl-1-piperidinyl)ethyl]acetonitrile

Product 1

HCID 12612308alpha-(o-Fluorophenyl)-alpha-[2-(diisopropylamino)ethyl]-alpha-[2-(2-methyl-1-piperidinyl)ethyl]acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 1118
Sulfuric Acid
Solvent

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

  1. temperatureThe resulting solution is heated on a steam bath for about 2 hours
  2. extractionThe alkaline solution is extracted with ether
  3. extractionthe ether extract
  4. dry with materialdried over calcium sulfate
  5. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes