Acetic Acid → HCID 22277813, compound

HRID 2055332Notes

Reaction equation

HRID 2055332 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2].C(O)(=O)C.[CH:13]1([NH2:16])[CH2:15][CH2:14]1.C([O-])(O)=O.[Na+]>CCOCC.O>[CH:13]1([NH:16][CH2:2][CH2:1][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 75024-VinylpyridineHCID 69828CyclopropylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 22277813HCID 22277813, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Vinyl pyridine (50 mmol), glacial acetic acid (3 ml), cyclopropylamine (4.28 g, 75 mmol) and water (12.8 ml) were heated at 50° C. for 22 hours. The crude reaction products were added to a vigorously stirred mixture of ether and saturated aqueous NaHCO3. After partitioning, the organic phase was washed with water, brine and dried. Filtered and solvents removed under vacuum. The residue was further distilled under vacuum (Kugelrohr) and the product amine collected. NMR (CDCl3) 8.45 (m, 2H), 7.05 (m, 2H), 2.93 (m, 2H), 2.73 (m, 2H), 2.07 (m, 1H), 1.37 (m, 2H), 1.25 (m, 2H); m/z 163.17.

Workup

  1. customThe crude reaction products
  2. customAfter partitioning
  3. washthe organic phase was washed with water, brine
  4. customdried
  5. filtrationFiltered
  6. customsolvents removed under vacuum
  7. distillationThe residue was further distilled under vacuum (Kugelrohr)
  8. customthe product amine collected

Sources & evidence

ORD record
ord-48bc9f47382e487cad453a233a0e2875
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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