Borohydride → 3-{[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl]amino}propan-1-ol

HRID 1193994Notes

Reaction equation

HRID 1193994 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[BH4-].[Na+].[BH4-]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 14156811HCID 14156811, compound

Product 1

HCID 141568923-{[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl]amino}propan-1-olYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

179.0 g (0.5737 mole) of 1-(2-(2,4-dichlorophenyl)-2-(3-hydroxypropylimino)ethyl)-1H-imidazole are dissolved in 300 ml of methanol, the solution is cooled to 0° C., and 50.0 g (1.322 mole) of sodium borohydride are added in portions in such a way that the temperature does not rise above 5° C. After the borohydride has been added, the reaction mixture is stirred at room temperature for a further 2 hours, then evaporated to dryness, and the pH is adjusted to 1 with half-concentrated hydrochloric acid. Subsequently, the reaction solution is adjusted to a pH of about 12 with 40% strength sodium hydroxide solution, and is extracted several times with dichloromethane. After the combined organic extracts have been washed with water and dried, and the solvent has been removed in vacuo, 169 g of crude product are obtained as an oil. Recrystallization of the oil from acetone results in 107 g of pure 1-(2-(2,4-dichlorophenyl)-2-(3-hydroxypropylamino)ethyl)-1H-imidazole of melting point 77°-79° C. (Yield: 51%).

Workup

  1. customdoes not rise above 5° C
  2. customevaporated to dryness
  3. extractionis extracted several times with dichloromethane
  4. washAfter the combined organic extracts have been washed with water
  5. customdried
  6. customthe solvent has been removed in vacuo, 169 g of crude product
  7. customare obtained as an oil
  8. customRecrystallization of the oil from acetone
  9. customresults in 107 g of pure 1-(2-(2,4-dichlorophenyl)-2-(3-hydroxypropylamino)ethyl)-1H-imidazole of melting point 77°-79° C. (Yield: 51%)

Sources & evidence

ORD record
ord-531bc0519c9f498396cfbbcf3bdd5538
Source dataset
uspto-grants-1989_03
Patent number
US04812465

Reaction notes

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