tert-butyl N-[2-(pyridin-2-ylamino)ethyl]carbamate → N~1~-(Pyridin-2-yl)ethane-1,2-diamine--hydrogen chloride (1/2)

HRID 989891Notes

Reaction equation

HRID 989891 reaction equation
[ClH:1].O1CCOCC1.C(OC([NH:15][CH2:16][CH2:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=O)(C)(C)C>C(Cl)Cl>[ClH:1].[ClH:1].[NH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 18419519tert-butyl N-[2-(pyridin-2-ylamino)ethyl]carbamateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 14238461N~1~-(Pyridin-2-yl)ethane-1,2-diamine--hydrogen chloride (1/2)Yield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 N HCl/dioxane (54 mL) was added in a stream to a solution of 2-[[2-(tert-butoxycarbonyl)amino-1-ethyl]amino]pyridine (5.09 g, 21.45 mmole) in anhydrous CH2Cl2 (54 mL) at 0° C. under argon, then the mixture was warmed to RT. After 2 hr, the mixture was cooled to 0° C. and suction filtered. The solid was washed extensively with anhydrous Et2O and dried in high vacuum at 40° C. to afford the title compound (4.27 g, 95%) as an off-white, somewhat hygroscopic solid: 1H NMR (400 MHz, CD3OD) δ7.99-8.07 (m, 1 H), 7.92-7.98 (m, 1 H), 7.19 (d, J=9.1 Hz, 1 H), 6.98-7.04 (m, 1 H), 3.76 (t,J=6.2 Hz, 2 H). 3.27 (t, J=6.2 Hz, 2 H, partially obscured by residual solvent signal); MS (ES) m/e 138 (M+H)+.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. filtrationsuction filtered
  3. washThe solid was washed extensively with anhydrous Et2O
  4. customdried in high vacuum at 40° C.

Sources & evidence

ORD record
ord-a460d4ed818e4d8493fba293027b1afd
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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