Hydrochloric Acid → HCID 178491092, compound

HRID 1620133Notes

Reaction equation

HRID 1620133 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:12]([NH2:14])[CH3:13])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:20]=O.[BH4-].[Na+].Cl.[OH-].[Na+]>CO>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:20][NH:14][CH:12]([C:9]1[NH:10][CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)[CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8419VeratraldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 178463402HCID 178463402, compound

Product 1

HCID 178491092HCID 178491092, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 1-(4-phenyl-1H-imidazol-2-yl)-ethylamine (0.061 g, 0.33 mmol) of Example 1, and 0.55 g (0.33 mmol) of 3,4-dimethoxybenzaldehyde in 5 mL of anhydrous methanol was stirred at room temperature for 1 h and then cooled to about 0-10° C. in an ice bath for 1 h. The reaction was treated carefully with 0.019 g (0.49 mmol) of sodium borohydride in one portion and maintained at about 0-10° C. for 21 h. Cold 2M aqueous HCl was added dropwise (30 drops), the mixture was stirred for 5 min, and then partially concentrated in vacuo unheated. The residual material was taken up in EtOAc to yield a suspension that was treated with 5 mL of cold 3M aqueous NaOH and stirred vigorously until clear. The phases were separated and the aqueous layer was extracted three times additional with EtOAc. The combined extracts were dried over MgSO4, filtered, and concentrated to afford 0.11 g of (3,4-dimethoxy-benzyl)-[1-(4-phenyl-1H-imidazol-2-yl)ethyl]-amine as a light yellow oil (HPLC: 87% @ 254 nm and 66% @ 214 nm). MS (ES+) (relative intensity): 338.1 (100) (M+1). This sample was of sufficient quality to use in the next reaction without further purification. The title compound may be substituted for Cpd 1d of Example 1 and elaborated to compounds of the present invention with the appropriate reagents, starting materials and purification methods known to those skilled in the art.

Workup

  1. temperaturemaintained at about 0-10° C. for 21 h
  2. concentrationpartially concentrated in vacuo unheated
  3. customto yield a suspension that
  4. stirringstirred vigorously until clear
  5. customThe phases were separated
  6. extractionthe aqueous layer was extracted three times additional with EtOAc
  7. dry with materialThe combined extracts were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9df7c772494c4d25aa11e91b2614e812
Source dataset
uspto-grants-2014_07
Patent number
US08772325B2

Reaction notes

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