Methylamine → HCID 15482079, compound

HRID 1358691Notes

Reaction equation

HRID 1358691 reaction equation
[CH:1]1([C:8]#[N:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=[CH:2]1.[OH-].[Na+].[CH3:12][NH2:13]>CO>[CH3:12][N:13]1[CH:5]2[CH2:4][CH2:3][CH:2]1[C:1]([C:8]#[N:9])=[CH:7][CH2:6]2

Participants

5

Reactant 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 1395162,4,6-Cycloheptatriene-1-carbonitrile

Product 1

HCID 15482079HCID 15482079, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
125 °C

Procedure

In 2 ml of methanol was dissolved 0.5 g (4.27 mmol) of 2,4,6-cycloheptatriene-1-carbonitrile (4: CHT-CN). A solution of 171 mg (4.27 mmol) of sodium hydroxide in 5 ml of methanol and then 3 ml (about 38 mmol) of 40% methanolic solution of methylamine were added thereto, and the resulting mixture was stirred with heating at 125° C. for 10 hours in a sealed vessel. After standing at room temperature, the methanol was evaporated and the residue was adjusted to pH 2 with 1N sulfuric acid solution, followed by extraction with chloroform (No. of run: 1) or ether (No. of run: 2 to 5) (separation into an organic layer 1 and an aqueous layer 1). The aqueous layer 1 was neutralized with 4N sodium hydroxide solution, followed by extraction with chloroform (No. of run: 1) or ether (No. of run: 2 to 5) (separation into an organic layer 2 and an aqueous layer 2). The organic layer 2 was dried and then the solvent was evaporated therefrom to obtain 0.458 g of a brown oil (1RS)-AECG-CN (yield: 70%).

Workup

  1. customAfter standing at room temperature
  2. customthe methanol was evaporated
  3. extractionfollowed by extraction with chloroform (No
  4. customof run: 2 to 5) (separation into an organic layer 1
  5. extractionfollowed by extraction with chloroform (No
  6. customof run: 2 to 5) (separation into an organic layer 2
  7. dry with materialThe organic layer 2 was dried
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d8faa37e93234cbe973607bd5eb3c6e8
Source dataset
uspto-grants-2003_07
Patent number
US06596868B2

Reaction notes

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