Cyclopropylamine → HCID 57495608, compound

HRID 1092340Notes

Reaction equation

HRID 1092340 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH:5]1([CH:8]=O)[CH2:7][CH2:6]1.C[Si]([C:14]#[N:15])(C)C>CCOCC>[CH:5]1([CH:8]([NH:4][CH:1]2[CH2:3][CH2:2]2)[C:14]#[N:15])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 82115Trimethylsilyl cyanideHCID 123114Cyclopropanecarboxaldehyde

Product 1

HCID 57495608HCID 57495608, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

Following a procedure outlined in Synth. Commun. 15(2), 1985, 157-163, cyclopropylamine (2 g) and cyclopropanecarboxaldehyde (4.9 g) were combined in a pressure tube and heated to 100° C. for 10 minutes. The mixture was cooled to RT and trimethylsilylcyanide (8.76 mL) was added carefully with cooling by means of an ice bath (exothermic!). After addition, the mixture was reheated to 100° C. for another 10 minutes. After cooling, the mixture was diluted with ether and extracted two times with 2 N HCl. The combined aqueous extracts were basified with conc. NaOH to pH 10, saturated with NaCl and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography using ethyl acetate/heptane 1:1 as an eluent to give the desired material as a colorless oil (884 mg). MS (EI): 137.2 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. temperaturewith cooling by means of an ice bath (exothermic!)
  3. additionAfter addition
  4. temperatureAfter cooling
  5. extractionextracted two times with 2 N HCl
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-eb0b4930c85146afaa35713ceb620728
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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