Hydrochloric Acid → HCID 58193743, compound

HRID 330714Notes

Reaction equation

HRID 330714 reaction equation
CO[C:3]([C:5]1([C:9]#[N:10])[CH2:8][CH2:7][CH2:6]1)=[O:4].[CH2:11]([NH2:14])[CH2:12][NH2:13].Cl>CO.O>[NH2:13][CH2:12][CH2:11][NH:14][C:3]([C:5]1([C:9]#[N:10])[CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 25918826Methyl 1-cyanocyclobutane-1-carboxylate

Product 1

HCID 58193743HCID 58193743, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of compound 1 (8.74 g, 0.063 mol) in CH3OH (50 mL) was added to ethylenediamine (3.77 g, 4.25 mL, 0.63 mol) at room temperature. After 15 h at room temperature, the mixture was evaporated. The yellow oil was obtained and dissolved in 20 mL of distilled water, acidulated with HCl to pH 2 and the solution applied to an AG 50W×8 column cation exchange column (200-400 mesh, H+ form, 100 mL of resin, 3.0 cm column diameter). The column was eluted first with H2O to remove excess ethylenediamine and then with a gradient HCl. The 0.5-1 N HCl solution containing the product was evaporated to dryness, yielding 6.37 g (60.47%). MS (ESI): m/z: 168.08 [M+H]+. Anal. Calcd (Found) for C8H13N3O: C, 57.46 (57.02); H, 7.84 (7.49); N, 25.13 (24.88). 1H NMR (D2O, 400 MHz), δ (ppm): 3.46 (t, J=6.0 Hz, 2H, —NHCH2CH2NH2), 3.07 (t, J=6.0 Hz, 2H, —NHCH2CH2NH2), 2.60-2.50 (m, 4H, —CCH2CH2CH2—), 1.94-2.14 (m, 2H, —CCH2CH2CH2—). 13C NMR (D2O, 400 MHz), δ (ppm): 168.99, 119.95, 41.39, 40.59, 39.38, 31.13, 17.09.

Workup

  1. customthe mixture was evaporated
  2. customThe yellow oil was obtained
  3. washThe column was eluted first with H2O
  4. customto remove excess ethylenediamine
  5. additionThe 0.5-1 N HCl solution containing the product
  6. customwas evaporated to dryness
  7. customyielding 6.37 g (60.47%)

Sources & evidence

ORD record
ord-f44a40a5660c41e38d6f90c597bca4b8
Source dataset
uspto-grants-2014_11
Patent number
US08877163B2

Reaction notes

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