Ethylamine → 4-[3-(Ethylamino)-2-hydroxypropoxy]-benzonitrile

HRID 466218Notes

Reaction equation

HRID 466218 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[CH2:14]([NH2:16])[CH3:15]>C(#N)C>[CH2:14]([NH:16][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[CH3:15]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 27643014-(2-Oxiranylmethoxy)benzenecarbonitrile

Product 1

HCID 150668414-[3-(Ethylamino)-2-hydroxypropoxy]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

86.0 g of 4-(oxiranylmethoxy) benzonitrile was dissolved in 250 ml acetonitrile and mixed with 29.7 g ethylamine in an autoclave. The mixture was heated in a boiling water-bath over night, evaporated and the residue was dissolved in 2-M hydrochloric acid. This acidic waterlayer was washed twice with ether, alkalized with 10-M sodium hydroxide and extracted with three portions of dichloromethane.

Workup

  1. temperatureThe mixture was heated in a boiling water-bath over night
  2. customevaporated
  3. dissolutionthe residue was dissolved in 2-M hydrochloric acid
  4. washThis acidic waterlayer was washed twice with ether
  5. extractionextracted with three portions of dichloromethane

Sources & evidence

ORD record
ord-4a26f771acd94d58a2cf9af214d0f416
Source dataset
uspto-grants-1992_10
Patent number
US05155133

Reaction notes

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