Ethylene Glycol → Ammonia

HRID 414618Notes

Reaction equation

HRID 414618 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Cl)=[CH:3][CH:2]=1.C(O)CO.[CH3:25][NH:26][CH3:27]>O>[NH3:26].[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:26]([CH3:27])[CH3:25])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 674DimethylamineHCID 21281389HCID 21281389, compound

Product 2

HCID 222AmmoniaHCID 21281219HCID 21281219, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(4-biphenyloxy)-6-chlorohexane (5.0 g) and ethylene glycol saturated with dimethylamine (60 ml), were heated at reflux for 3 hours using a dry ice condenser. The solution was added to water. The resulting mixture was extracted with ethyl acetate, dried with sodium sulfate and evaporated. The crude product was chromatographed on silica gel, eluting with a solution of dichloromethane:methanolic ammonia (95:5), to yield 6-(4-biphenyloxy)-1-dimethylaminohexane, which was converted to the hydrochloride salt, m.p. 163°-165° C.

Workup

  1. temperatureat reflux for 3 hours
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. customevaporated
  5. customThe crude product was chromatographed on silica gel
  6. washeluting with a solution of dichloromethane

Sources & evidence

ORD record
ord-5aecfdafc84f4ef0a0a5ff61d2bfdac1
Source dataset
uspto-grants-1988_12
Patent number
US04792570

Reaction notes

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