Benzaldehyde → HCID 14712103, compound

HRID 2177545Notes

Reaction equation

HRID 2177545 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CO.[BH4-].[Na+]>CCO>[CH2:9]([NH:1][CH2:2][CH2:3][C:4]1[NH:8][CH:7]=[N:6][CH:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 887MethanolHCID 4311764Sodium borohydrideHCID 178419017HCID 178419017, compound

Product 1

HCID 14712103HCID 14712103, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound XIIIA is prepared by treatment of a mixture of compound XIIA, histamine, and benzaldehyde in a solvent such as MeOH or EtOH, with a reducing agent such as NaBH4 to provide N-benzyl-2-(1H-imidazol-5-yl)ethanamine (compound not shown). To this compound in water at 0° C., is added KOH followed by acetaldehyde. After approximately six hours at 80° C. followed by treatment with acid, compound XIIIA, PG=Bn, is isolated. Trifluoromethyl derivative XIVA is also prepared from compound XIIA. To a solution of compound XIIA in a solvent such as water at a temperature of about 0° C., is added a base such as KOH along with trifluoroacetaldehyde. After heating at a temperature of approximately 80° C. for approximately 6 hours and acidification, compound XIVA is isolated.

Sources & evidence

ORD record
ord-7c6ab23cafe844dbb784c255d3711865
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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