Phenylacetyl chloride → N-(2-amino-2-methylpropyl)-2-phenylacetamide

HRID 223503Notes

Reaction equation

HRID 223503 reaction equation
[CH3:1][C:2]([CH3:6])([NH2:5])[CH2:3][NH2:4].[C:7]1([CH2:13][C:14](Cl)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[CH3:1][C:2]([NH2:5])([CH3:6])[CH2:3][NH:4][C:14](=[O:15])[CH2:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 131282-Methylpropylenediamine

Product 1

HCID 12876178N-(2-amino-2-methylpropyl)-2-phenylacetamideYield 63.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1,1-dimethylethylenediamine (8.8 g.) in ether (250 ml.) was added during 2 hours to a stirred solution of phenylacetyl chloride (15.4 g.) in ether (250 ml.). This mixture was further stirred for 2 hours. The solid was separated by filtration, and dissolved in warm water (150 ml.). The solution obtained was filtered. The filtrate was basified by addition of an excess of saturated aqueous sodium carbonate solution (50 ml.), and then extracted with chloroform (3×250 ml.). The extracts were dried (MgSO4) and evaporated to give an oil which crystallised on addition of a 1:1 v/v mixture of ether and petrol (60°-80°) to give 1,1-dimethyl-2-(2-phenylacetamido)ethylamine (13.1 g., 63%), m.p. 47°-48° C.

Workup

  1. customThe solid was separated by filtration
  2. dissolutiondissolved in warm water (150 ml.)
  3. customThe solution obtained
  4. filtrationwas filtered
  5. additionThe filtrate was basified by addition of an excess of saturated aqueous sodium carbonate solution (50 ml.)
  6. extractionextracted with chloroform (3×250 ml.)
  7. dry with materialThe extracts were dried (MgSO4)
  8. customevaporated
  9. customto give an oil which
  10. customcrystallised on addition of a 1:1 v/v mixture of ether and petrol (60°-80°)

Sources & evidence

ORD record
ord-7ec158d019ce4fc897b2a618c73c7c8d
Source dataset
uspto-grants-1982_10
Patent number
US04355045

Reaction notes

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