Formamidine acetate → HCID 178420898, compound

HRID 1159174Notes

Reaction equation

HRID 1159174 reaction equation
[C:1]1([CH2:7][C@@H:8]([NH2:11])[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](O)(=O)C.C(N)=N>C(O)C>[CH2:7]([C@@H:8]1[CH2:9][NH:10][CH:12]=[N:11]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 12699299(2R)-3-Phenylpropane-1,2-diamine

Product 1

HCID 178420898HCID 178420898, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R)-3-phenyl-1,2-propanediamine (0.20 g, 1.33 mmol) in ethanol (5 ml) was added formamidine acetate (0.15 g, 1.45 mmol) and the mixture was stirred overnight at room temperature. The solvent was evaporated, sodium hydroxide (2N, 5 ml) was added and the mixture was extracted 3 times with dichloromethane (10 ml). The combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent:ethyl acetate/methanol=90:10) to yield a colorless oil (0.20 g, 92%); MS (ISP): 161.4 ((M+H)+).

Workup

  1. customThe solvent was evaporated
  2. additionsodium hydroxide (2N, 5 ml) was added
  3. extractionthe mixture was extracted 3 times with dichloromethane (10 ml)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent:ethyl acetate/methanol=90:10)

Sources & evidence

ORD record
ord-0187ccd68ae8458c8f42c19f3058b348
Source dataset
uspto-grants-2010_10
Patent number
US07812047B2

Reaction notes

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