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Dimethylformamide → HCID 21496591, compound

HRID 1730825
Notes
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Reaction equation

HRID 1730825 reaction equation
[CH2:1]([O:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH2:7]Cl)[CH3:2].[CH2:16]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[O:21][CH2:22][CH2:23][NH2:24])[CH3:17].[C:29](=[O:32])([OH:31])[O-].[Na+].CN(C)C=O>O>[C:4]([OH:3])(=[O:18])[C:29]([OH:31])=[O:32].[CH2:1]([O:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH2:7][NH:24][CH2:23][CH2:22][O:21][C:20]1[CH:25]=[CH:26][CH:27]=[CH:28][C:19]=1[O:18][CH2:16][CH3:17])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 53030422-(2-Ethoxyphenoxy)ethylamineHCID 21496613HCID 21496613, compound

Product 1

HCID 21496591HCID 21496591, compound

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4.4 g of 4-ethoxy-4-(4-fluorophenyl)-butyl chloride, 3.6 g of 2-(2-ethoxyphenoxy)ethylamine, 2 g of sodium bicarbonate and 44 ml of N,N-dimethylformamide was stirred at about 110° C for 20 hours. After cooling, the reaction mixture was poured into cold water and extracted with benzene. The benzene layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The oily residue was treated with ethanolic oxalic acid and recrystallized from ethanol to give N-[4-ethoxy-4-(4-fluorophenyl)butyl]-2-(2-ethoxyphenoxy)-ethylamine oxalate, M.P. 157° - 160° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with benzene
  3. washThe benzene layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe oily residue was treated with ethanolic oxalic acid
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b06bd60d568b4661af8b5941a6d78a76
Source dataset
uspto-grants-1976_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03993780

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes