2-Chloroethyldiisopropylammonium chloride → 2-Propanamine, N-(2-(2-butoxyphenoxy)ethyl)-N-(1-methylethyl)-

HRID 616370

Reaction equation

HRID 616370 reaction equation
[Na].[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])[CH2:3][CH2:4][CH3:5].Cl.[CH:15]([N:18]([CH2:22][CH2:23]Cl)[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16]>C(O)C>[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:23][CH2:22][N:18]([CH:19]([CH3:21])[CH3:20])[CH:15]([CH3:17])[CH3:16])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 779422-Chloroethyldiisopropylammonium chlorideHCID 5360545Sodium2×HCID 12447746o-Butoxyphenol

Product 1

HCID 30426722-Propanamine, N-(2-(2-butoxyphenoxy)ethyl)-N-(1-methylethyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 750 ml of absolute ethanol was added gradually 13.8 g (0.60 mole) of metallic sodium cut into pieces. After all the sodium had reacted 49.8 g (0.30 mole) of o-butoxyphenol was added. The solution was cooled down in ice-water whereupon a solution of 60.0 g (0.30 mole) of diisopropylaminoethylchloride hydrochloride in 150 ml of absolute ethanol was added rapidly with stirring. The reaction mixture was then boiled under reflux for 5 hours.

Workup

  1. additionwas added
  2. additionwas added rapidly
  3. temperatureunder reflux for 5 hours

Sources & evidence

ORD record
ord-e3e95e7300674abbb8792069d63bc213
Source dataset
uspto-grants-1978_02
Patent number
US04073917

Linked notes

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