Hydrochloric Acid → HCID 53805374, compound

HRID 2399155Notes

Reaction equation

HRID 2399155 reaction equation
[NH2:1][CH2:2][CH:3]([OH:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].O=[C:15]([CH3:27])[CH2:16][O:17][C:18]1[C:19]([C:24]([NH2:26])=[O:25])=[N:20][CH:21]=[CH:22][CH:23]=1.[BH4-].[Na+].Cl>C(O)C>[CH3:27][CH:15]([NH:1][CH2:2][CH:3]([OH:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])[CH2:16][O:17][C:18]1[C:19]([C:24](=[O:25])[NH2:26])=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 655736HCID 655736, compoundHCID 4311764Sodium borohydrideHCID 54100482HCID 54100482, compound

Product 1

HCID 53805374HCID 53805374, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.5 g of 1-amino-3-(2-methyl-phenyloxy)-2-propanol and 4.85 g of 3-(2-oxo-propyloxy)-2-pyridinecarboxylic acid amide in 100 ml of ethanol is heated under reflux for 3 hours. After cooling to room temperature, 1.9 g of sodium borohydride are added whilst stirring; the temperature gradually rises to 45° C. After the reaction has subsided, the mixture is stirred for a further hour. The reaction mixture is then acidified with 2 N hydrochloric acid whilst cooling, and is extracted with 20 ml of ethyl acetate. The aqueous phase is rendered alkaline with a concentrated aqueous sodium hydroxide solution and is extracted with three times 50 ml of ethyl acetate. After drying over sodium sulphate and evaporation of the organic solution, oily, crude 1-[1-methyl-2-(2-carbamoyl-3-pyridyloxy)-ethyl-amino]-3-(2-methyl-phenyloxy)-2-propanol is obtained, which forms a neutral fumaric acid salt, melting point 145°-161° C. after recrystallisation from a mixture of methanol and ethyl methyl ketone.

Workup

  1. temperatureunder reflux for 3 hours
  2. customgradually rises to 45° C
  3. stirringthe mixture is stirred for a further hour
  4. temperaturewhilst cooling
  5. extractionis extracted with 20 ml of ethyl acetate
  6. extractionis extracted with three times 50 ml of ethyl acetate
  7. dry with materialAfter drying over sodium sulphate and evaporation of the organic solution

Sources & evidence

ORD record
ord-7ea91f8f4bea4910b46476aada01f15b
Source dataset
uspto-grants-1977_05
Patent number
US04027027

Reaction notes

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