Benzylamine → HCID 22033754, compound

HRID 1791985Notes

Reaction equation

HRID 1791985 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:9]#[N:10].[K+].S(=O)(O)[O-].[Na+].[C:17]1([CH:22]=[O:23])([CH:20]=O)[CH2:19][CH2:18]1.C(=O)(O)[O-].[Na+]>C(O)C.O.C(OCC)(=O)C.CCCCCC>[CH2:1]([NH:8][CH:20]([C:17]1([CH:22]=[O:23])[CH2:19][CH2:18]1)[C:9]#[N:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 7504BenzylamineHCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 220337631,1-CyclopropanedicarboxaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 22033754HCID 22033754, compoundYield 50.9%

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzylamine (107 mg, 1.0 mmol) was suspended in a mixture of ethanol (0.5 ml) and water (1.5 ml). To the resulting suspension were successively added potassium cyanide (65 mg, 1.0 mmol) and sodium bisulfite (104 mg, 1.0 mmol) under ice cooling and stirring. An ethanol (1.5 ml) solution of 1,1-cyclopropane dicarboaldehyde (98 mg, 1.0 mmol) was added dropwise and the mixture was stirred at the same temperature for 2 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over sodium sulfate, filtered, and then evaporated under reduced pressure. The oily residue thus obtained was subjected to chromatography on a silica gel column (silica gel 8.0 g; hexane:ethyl acetate=5:1), whereby the title compound (109 mg, 50.8%) was obtained as a slightly yellow oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated saline
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe oily residue thus obtained

Sources & evidence

ORD record
ord-608867c614f7451cb92cc5962df472bd
Source dataset
uspto-grants-2006_07
Patent number
US07074837B2

Reaction notes

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