Benzaldehyde → HCID 14712103, compound

HRID 2177555Notes

Reaction equation

HRID 2177555 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.[BH4-].[Na+]>CO>[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

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 178419017HCID 178419017, compound

Product 1

HCID 14712103HCID 14712103, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of histamine (free base) (1.00 g, 9.0 mmol) and benzaldehyde (0.91 mL, 9.0 mmol) in MeOH (25 mL) was stirred at rt for 30 min. To this solution was slowly added NaBH4 (0.21 g, 5.4 mmol). The reaction was let stir for 3 h, quenched with a minimal amount of H2O and concentrated. The residue was dissolved in EtOH and filtered through Celite©. The solvent was concentrated to give the title product (1.50 g, 83%). MS (ESI): mass calculated for C12H15N3, 201.1. m/z found 202.2 [M+H]+.

Workup

  1. customquenched with a minimal amount of H2O
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOH
  4. filtrationfiltered through Celite©
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-364da8426544476cb3324971286145a3
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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