Phenol → Ethanamine, N,N-diethyl-2-phenoxy-

HRID 1855319Notes

Reaction equation

HRID 1855319 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH2:8][CH3:9])[CH2:6][CH3:7].[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>O>[CH2:6]([N:5]([CH2:8][CH3:9])[CH2:4][CH2:3][O:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:7]

Participants

5

Reactant 3

HCID 996PhenolHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 66150Ethanamine, N,N-diethyl-2-phenoxy-Yield 79.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 108.5 g (0.630 mol; 1.2 eq.) of N-(2-chloroethyl)-N,N-diethylamine hydrochloride in 65 ml of water is added slowly (over about 55 minutes) to a mixture containing 50 g (0.531 mol) of phenol and 46.3 g (1.158 mol; 2.2 eq.) of NaOH in 270 ml of water. The mixture is stirred for 3 hours 30 minutes at 20° C. and then for 45 minutes at 55° C. The phases are separated by settling and the supernatant oil diluted in 100 ml of DCE is washed with (i) 100 ml of 2.5% sodium hydroxide and then (ii) with 100 ml of 5% sodium hydroxide. The product is dried over sodium sulfate and then concentrated. 81.4 g of crude N,N-diethyl-N-(phenoxyethyl)amine are obtained.

Workup

  1. waitfor 45 minutes at 55° C
  2. customThe phases are separated
  3. additionthe supernatant oil diluted in 100 ml of DCE
  4. washis washed with (i) 100 ml of 2.5% sodium hydroxide
  5. dry with materialThe product is dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31d7aa2457a04fbd899bcbfad84adc8d
Source dataset
uspto-grants-2015_02
Patent number
US08962869B2

Reaction notes

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