2-Amino-2-methyl-1-propanol → (+/-)-N-(beta-Hydroxy-alpha,alpha-dimethylethyl)-2-[4-(4-chlorophenoxy)-phenoxy]-1-propylamine hydrochloride

HRID 263084Notes

Reaction equation

HRID 263084 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][C:25]([CH3:29])([CH3:28])[CH2:26][OH:27]>O>[ClH:23].[OH:27][CH2:26][C: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])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 21318102(+/-)-2-[4-(4-Chlorophenoxy)-phenoxyl]-propyl mesylate

Product 1

HCID 21318059(+/-)-N-(beta-Hydroxy-alpha,alpha-dimethylethyl)-2-[4-(4-chlorophenoxy)-phenoxy]-1-propylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 13 g (0.0365 mol) of the mesylate of Example 34 and of 32.5 g (0.365 mol) of 2-amino-2-methyl-1-propanol is heated slowly to 170° C. The reaction mixture is allowed to return to ambient temperature and is taken up in water. The insoluble matter is extracted with diethyl ether and the organic phase obtained is washed with water and dried over dry sodium sulphate to give, after evaporation of the solvent, 12.7 g of a limpid pale yellow oil. After treating 12 g of this oil in a solution of hydrogen chloride in diethyl ether, and purifying the product by crystallisation from ethyl acetate, 11.2 g of a white powder which is soluble in water to the extent of 200 g/l are obtained.

Workup

  1. customto return to ambient temperature
  2. extractionThe insoluble matter is extracted with diethyl ether
  3. customthe organic phase obtained
  4. washis washed with water
  5. dry with materialdried over dry sodium sulphate
  6. customto give
  7. customafter evaporation of the solvent, 12.7 g of a limpid pale yellow oil
  8. additionAfter treating 12 g of this oil in a solution of hydrogen chloride in diethyl ether
  9. custompurifying the product
  10. customby crystallisation from ethyl acetate, 11.2 g of a white powder which
  11. customare obtained

Sources & evidence

ORD record
ord-448834a064344ffd8126315ed70cf19e
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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