Ethanolamine → (+/-)-N-Hydroxyethyl-2-[4-(4-chlorophenoxy)-phenoxy]-1-propylamine hydrochloride

HRID 263083Notes

Reaction equation

HRID 263083 reaction equation
S(O[CH2:6][CH:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)[CH3:8])(=O)(=O)C.[NH2:24][CH2:25][CH2:26][OH:27]>O>[ClH:23].[OH:27][CH2:26][CH2:25][NH:24][CH2:6][CH:7]([O:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[CH:14][CH:15]=1)[CH3:8]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 21318102(+/-)-2-[4-(4-Chlorophenoxy)-phenoxyl]-propyl mesylate

Product 1

HCID 21318077(+/-)-N-Hydroxyethyl-2-[4-(4-chlorophenoxy)-phenoxy]-1-propylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 10 g (0.028 mol) of the mesylate of Example 34 and of 17 g (0.280 mol) of 2-aminoethanol is slowly heated to 170° C. The reaction mixture is allowed to return to ambient temperature and is taken up in water. After extracting the insoluble matter with diethyl ether, washing the organic phase with water and drying it over dry sodium sulphate, 8.7 g of a pale yellow oil are obtained after evaporation of the solvent. 8.4 g of this product, in ethyl acetate, are treated with a solution of hydrogen chloride in ether and the product is then purified by crystallisation from a mixture of ethyl acetate and anhydrous ethanol (7:2 by volume) to give 8.3 g of white flakes which are soluble in water to the extent of 200 g/l.

Workup

  1. customto return to ambient temperature
  2. extractionAfter extracting the insoluble matter with diethyl ether
  3. washwashing the organic phase with water
  4. dry with materialdrying it over dry sodium sulphate, 8.7 g of a pale yellow oil
  5. customare obtained
  6. customafter evaporation of the solvent
  7. addition8.4 g of this product, in ethyl acetate, are treated with a solution of hydrogen chloride in ether
  8. customthe product is then purified by crystallisation from a mixture of ethyl acetate and anhydrous ethanol (7:2 by volume)
  9. customto give 8.3 g of white flakes which

Sources & evidence

ORD record
ord-2c76e7728b3848058b1fb19df9af6f84
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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