1H-imidazole-2-carbaldehyde → 1-(4-chlorophenyl)-N-(imidazol-2-ylmethyl)-1-methylethylamine

HRID 323968Notes

Reaction equation

HRID 323968 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH2:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1.[CH:13]([C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)=O.[BH4-].[Na+]>[OH-].[Na+].C(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH:12][CH2:13][C:15]2[NH:16][CH:17]=[CH:18][N:19]=2)([CH3:10])[CH3:11])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 451583372-(4-Chlorophenyl)propan-2-amine hydrochloride

Product 1

HCID 542318951-(4-chlorophenyl)-N-(imidazol-2-ylmethyl)-1-methylethylamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1-(4-chlorophenyl)-1-methylethylamine hydrochloride (2.7 g) was dissolved in 2M sodium hydroxide solution (50 ml) and the amine free base was extracted into diethyl ether to give an oil. This oil was dissolved in absolute ethanol (15 ml) and 2-formylimidazole (1.5 g) in absolute ethanol (20 ml) was added dropwise. The mixture was boiled under reflux for 4 hours and then left to stand at ambient temperature for 48 hours. Sodium borohydride (0.67 g) was added in portions to the solution and the mixture was boiled under reflux with stirring for 7 hours. The ethanol was removed under reduced pressure and water (40 ml) added to the residue. The mixture was filtered to give 1-(4-chlorophenyl)-N-(imidazol-2-ylmethyl)-1-methylethylamine, m.p. 164-165° C.

Workup

  1. extractionthe amine free base was extracted into diethyl ether
  2. customto give an oil
  3. temperatureunder reflux for 4 hours
  4. waitleft
  5. temperatureunder reflux
  6. customThe ethanol was removed under reduced pressure and water (40 ml)
  7. additionadded to the residue
  8. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-fec0e6eb738d4a5d8f5cb261516898ca
Source dataset
uspto-grants-2001_04
Patent number
US06215001B1

Reaction notes

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