Benzhydryl 2-chloroethyl ether → 2-(diphenylmethoxy)ethyl-N-methyl-N'-methylpropanediamine

HRID 129729Notes

Reaction equation

HRID 129729 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][CH2:9][CH2:10]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][NH:19][CH:20]([NH:23][CH3:24])[CH2:21][CH3:22]>C1(C)C=CC=CC=1>[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:8][CH2:9][CH2:10][C:20]([NH:23][CH3:24])([NH:19][CH3:18])[CH2:21][CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 141724Benzhydryl 2-chloroethyl etherHCID 22287041HCID 22287041, compound

Product 1

HCID 217598692-(diphenylmethoxy)ethyl-N-methyl-N'-methylpropanediamineYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3 g (12.2 mmole) of 2- (diphenyl-methoxy)ethyl chloride, 5 g (49 mmole) of N,N' -dimethyl-propanediamine and 40 ml of toluene was heated under reflux overnight. At the end of this time, the toluene layer was separated and washed with water; 25 ml of a 10% w/v aqueous solution of acetic acid was then added thereto. The aqueous layer was separated, and a 10% w/v aqueous solution of sodium hydroxide was added to make it alkaline. The mixture was then extracted with diethyl ether, and the solvent was removed by distillation under reuced pressure, to obtain 2.4 g (yield 63%) of the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customAt the end of this time, the toluene layer was separated
  4. washwashed with water
  5. addition25 ml of a 10% w/v aqueous solution of acetic acid was then added
  6. customThe aqueous layer was separated
  7. additiona 10% w/v aqueous solution of sodium hydroxide was added
  8. extractionThe mixture was then extracted with diethyl ether
  9. customthe solvent was removed by distillation under reuced pressure

Sources & evidence

ORD record
ord-02b3f8aa00f246cba28b781a2959ff3d
Source dataset
uspto-grants-1995_11
Patent number
US05470851

Reaction notes

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