Hydrochloric Acid → HCID 86732161, compound

HRID 930335Notes

Reaction equation

HRID 930335 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH:7]=2)[CH2:3][CH2:2]1.Cl>O1CCOCC1>[CH:1]1([C:4]#[C:5][C:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86732160HCID 86732160, compound

Product 1

HCID 86732161HCID 86732161, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a rt solution of tert-butyl 4-(cyclopropylethynyl)-5,6-dihydropyridine-1(2H)-carboxylate (0.344 g, 1.391 mmol) in 1,4-dioxane (4.0 mL) was added hydrogen chloride, 4.0 m solution in 1,4-dioxane (4.0 mL, 16.00 mmol) dropwise via syringe resulting in a dark brown solution. After 2 h the solvent was removed in vacuo and the residue was dissolved in DCM and washed with satd. NaHCO3. The organic solution was dried over MgSO4, filtered and concentrated to dryness to give 4-(cyclopropylethynyl)-1,2,3,6-tetrahydropyridine as a brown tar (186 mg, 91%).

Workup

  1. customresulting in a dark brown solution
  2. customAfter 2 h the solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with satd
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4b4b90490ecb4b37889b74f9c487cd98
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

Loading…