Hydrochloric Acid → N~1~-(Pyridin-2-yl)ethane-1,2-diamine--hydrogen chloride (1/2)

HRID 636300Notes

Reaction equation

HRID 636300 reaction equation
[ClH:1].C([NH:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)(OC(C)(C)C)=O>O1CCOCC1.C(Cl)Cl>[ClH:1].[ClH:1].[NH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18419519tert-butyl N-[2-(pyridin-2-ylamino)ethyl]carbamate

Product 1

HCID 14238461N~1~-(Pyridin-2-yl)ethane-1,2-diamine--hydrogen chloride (1/2)

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

4 N HCl in dioxane (3.2 mL) was added in a stream to a solution of 2-[[2-(Boc-amino)ethyl]amino]pyridine (148.4 mg, 0.63 mmole) in anhydrous CH2Cl2 (3.2 mL) at 0° C., then the reaction was warmed to RT. After 2 hr, the mixture was suction filtered to collect the precipitated solid, which was washed with anhydrous Et2O and dried to afford the title compound (132.8 mg, quantitative) as a yellow solid: 1H NMR (400, CD3OD) δ 7.99-8.07 (m, 1H), 7.92-7.98 (m, 1H), 7.19 (d, J=9.1 Hz, 1H), 6.98-7.04 (m, 1H), 3.76 (t, J=6.2 Hz, 2H), 3.27 (t, J=6.2 Hz, 2H, partially obscured by residual solvent signal); MS (ES) m/e 138 (M+H)+.

Workup

  1. filtrationfiltered
  2. customto collect the precipitated solid, which
  3. washwas washed with anhydrous Et2O
  4. customdried

Sources & evidence

ORD record
ord-947810ce16e94f99856010b8a95c01d0
Source dataset
uspto-grants-2001_02
Patent number
US06191304B1

Reaction notes

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