Formaldehyde → (2-Azabicyclo[2.2.1]hept-5-en-2-yl)acetonitrile

HRID 1975253Notes

Reaction equation

HRID 1975253 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[N:5].[CH2:6]=O.[CH:8]1[CH2:12][CH:11]=[CH:10][CH:9]=1>O.C(Cl)Cl>[CH:9]12[CH2:8][CH:12]([CH:11]=[CH:10]1)[CH2:6][N:5]2[CH2:4][C:3]#[N:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 7612CyclopentadieneHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 19101380(2-Azabicyclo[2.2.1]hept-5-en-2-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of aminoacetonitrile hydrochloride (18.5 g, 0.20 mol) in water at 5° C. is treated with 37% formalin (23.0 g, 0.28 mol formaldehyde) followed by cyclopentadiene (26.0 g, 0.4 mol), stirred at 5°-10° C. for 30 minutes and diluted with methylene chloride. The phases are separated, the aqueous phase is extracted with methylene chloride and basified to pH >12 with 10% NaOH. The aqueous basic phase is extracted with methylene chloride. The methylene chloride extract of the basic aqueous phase is concentrated in vacuo to give the title product (N-cyanomethylazanorbornene), 22.7 g, which can be distilled at 68°-70° C./0.55 torr. The compound is identified by NMR and mass spectral analyses.

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted with methylene chloride and basified to pH >12 with 10% NaOH
  3. extractionThe aqueous basic phase is extracted with methylene chloride
  4. extractionThe methylene chloride extract of the basic aqueous phase
  5. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-999ca333a69d48c5b13f029b14914a50
Source dataset
uspto-grants-1994_02
Patent number
US05284970

Reaction notes

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