Acetone → HCID 178457142, compound

HRID 1913553Notes

Reaction equation

HRID 1913553 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][C:16]([CH3:18])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH:16]([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])([CH3:18])[CH3:15]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 178463402HCID 178463402, compound

Product 1

HCID 178457142HCID 178457142, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-(4-Phenyl-1H-imidazol-2-yl)-ethylamine (0.20 g, 1.07 mmol) and acetone (0.062 g, 1.07 mmol) were mixed in 1,2-dichloroethane (4 mL), followed by the addition of NaBH(OAc)3 (0.34 g, 1.61 mmol). The resulting mixture was stirred at rt for 3 h. The reaction was quenched with saturated NaHCO3 solution. The mixture was extracted with EtOAc and the combined extracts were dried over Na2SO4. Filtration followed by evaporation to dryness under reduced pressure gave the crude isopropyl-[1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-amine (0.23 g, 100%) which was used for the next reaction without further purification. 1H NMR (300 MHz, CDCl3): δ 1.10 (3H, d), 1.18 (3H, d), 1.57 (3H, d), 2.86 (1H, m), 4.32 (1H, m), 7.24 (2H, m), 7.36 (2H, m), 7.69 (2H, m). MS (ES+): 230.2 (100%).

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe combined extracts were dried over Na2SO4
  4. filtrationFiltration
  5. customfollowed by evaporation to dryness under reduced pressure

Sources & evidence

ORD record
ord-dad6aad7bdba420bbe184f738127c18e
Source dataset
uspto-grants-2013_12
Patent number
US08609709B2

Reaction notes

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