Acetone → HCID 14976679, compound

HRID 2177579Notes

Reaction equation

HRID 2177579 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[CH3:9][C:10]([CH3:12])=O>CC(O)=O>[CH3:9][C:10]1([CH3:12])[C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH2:3][CH2:2][NH:1]1

Participants

4

Reactant 2

HCID 180AcetoneHCID 178419017HCID 178419017, compound

Product 1

HCID 14976679HCID 14976679, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of histamine (500 mg, 4.5 mmol) and acetone (3.3 mL, 45 mmol) in AcOH (3 mL) was heated at 100° C. overnight. The crude reaction mixture was concentrated and purified on 16 g SiO2 column with 0-80% NH3/MeOH CH2Cl2 to give the desired compound (543 mg, 80%). MS (ESI): mass calcd. for C8H13N3, 151.1. m/z found, 152.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.44 (s, 1H), 3.16 (t, J=5.7 Hz, 2H), 2.61 (t, J=5.7 Hz, 2H), 1.43 (s, 6H).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. custompurified on 16 g SiO2 column with 0-80% NH3/MeOH CH2Cl2

Sources & evidence

ORD record
ord-99bfef87ae7b4981813ae56616a89ba1
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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