Hydrochloric Acid → (5-Methanesulfonyl-pyridin-2-yl)-piperidin-4-yl-amine

HRID 913148Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:24][S:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[N:16][CH:17]=1)(=[O:22])=[O:23]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 4-(5-methanesulfonyl-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.00 g, 2.8 mmol, 1.0 equiv) in ethanol (18 mL) was added 4 M HCl in dioxane (3.52 mL, 14.1 mmol, 5.0 equiv) drop by drop and the reaction mixture stirred at 50° C. for 2 h. It was then cooled down to rt, poured into ice water and the pH adjusted to 9-10 by addition of a sat. solution of potassium carbonate. The solution was extracted six times with a mixture of dichloromethane/isopropanol (4:1). The combined organic layers were concentrated by evaporation under reduced pressure and the crude product was purified by crystallization from heptane to give 0.53 g (74%) of the title compound as colorless solid. MS (ISP): 256.2 [M+H]+.

Workup

temperatureIt was then cooled down to rt
extractionThe solution was extracted six times
additionwith a mixture of dichloromethane/isopropanol (4:1)
concentrationThe combined organic layers were concentrated by evaporation under reduced pressure
customthe crude product was purified by crystallization from heptane

Sources & evidence

ORD record: ord-dc3899b554124303b495f577a7b10bfe
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026255B2

Reaction notes

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