Formamidine acetate → HCID 178435739, compound

HRID 1159184Notes

Reaction equation

HRID 1159184 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([CH2:13][CH:14]([NH2:17])[CH2:15][NH2:16])=[CH:10][CH:9]=[CH:8]2)[CH3:2].[C:18](O)(=O)C.C(N)=N>CCO>[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([CH2:13][CH:14]1[CH2:15][NH:16][CH:18]=[N:17]1)=[CH:10][CH:9]=[CH:8]2)[CH3:2]

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 575431993-(8-Ethyl-naphthalen-1-yl)-propane-1,2-diamine

Product 1

HCID 178435739HCID 178435739, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(8-ethyl-naphthalen-1-yl)-propane-1,2-diamine (60 mg) in EtOH (6 ml) was treated at r.t. under an argon atmosphere with formamidine acetate (30 mg). The reaction mixture was stirred at r.t. overnight, then concentrated. The crude product was purified by column chromatography (silica gel; eluent: CH2Cl2→CH2Cl2/MeOH 9:1) to give (RS)-4-(8-ethyl-naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole (38 mg) as light yellow gum. MS (ISP): 239.3 ((M+H)+).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by column chromatography (silica gel; eluent: CH2Cl2→CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-dbb51d7f49384948ad7b6168a2413755
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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