Hydrochloric Acid → N2-(2,6-Dimethyl-4-pyridyl)propane-1,2-diamine hydrochloride

HRID 333082Notes

Reaction equation

HRID 333082 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]([CH3:19])[CH2:10][NH:11]C(=O)OC(C)(C)C)[CH:5]=[C:4]([CH3:20])[N:3]=1.[ClH:21]>O1CCOCC1>[ClH:21].[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]([CH3:19])[CH2:10][NH2:11])[CH:5]=[C:4]([CH3:20])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86691169Tert-butyl 2-(2,6-dimethylpyridin-4-ylamino)propylcarbamate

Product 1

HCID 66835507N2-(2,6-Dimethyl-4-pyridyl)propane-1,2-diamine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To tert-butyl 2-(2,6-dimethylpyridin-4-ylamino)propylcarbamate (147 mg, 0.526 mmol) dissolved in 1,4-dioxane (1 ml) a 4N solution of HCl in dioxane (2 ml, 8.00 mmol) was added. Within a few minutes a precipitate started to form. The solvent was removed in a stream of nitrogen, to the residue was added diethylether and the mixture was allowed to stand at room temperature overnight. The solvent was filtered off, the residue was dried under reduced pressure to yield 135 mg of an off-white solid MS (ESI) m/z=180.0.

Workup

  1. additionwas added
  2. waitWithin a few minutes a precipitate started
  3. customto form
  4. customThe solvent was removed in a stream of nitrogen, to the residue
  5. additionwas added diethylether
  6. filtrationThe solvent was filtered off
  7. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-23b3de78bbb24b248281e8b8438fb5c3
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

Loading…