Hydrochloric Acid → 6-(2,6-Dimethyl-piperidin-1-ylmethyl)-pyridin-2-ylamine

HRID 460197Notes

Reaction equation

Cl.C(OC(=O)[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]2[CH:21]([CH3:22])[CH2:20][CH2:19][CH2:18][CH:17]2[CH3:23])[N:10]=1)(C)(C)C.[OH-].[Na+]>CO>[CH3:23][CH:17]1[CH2:18][CH2:19][CH2:20][CH:21]([CH3:22])[N:16]1[CH2:15][C:11]1[N:10]=[C:9]([NH2:8])[CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 40 °C

Procedure

HCl (1.25 mL, 1.25 mmol) in MeOH (15 mL) was added to [6-(2,6-dimethyl-piperidin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (200 mg, 0.63 mmol) followed by heating at 40° C. for 18 h. The resulting mixture was cooled to RT and basified to pH 9 with 2 N NaOH. The mixture was extracted with CHCl3 (3×20 mL). The combined organic layers was dried over MgSO4 and concentrated in vacuo to give a yellow oil. MS m/z: 220.2 (M+H). Calc'd. for C13H21N3-219.17.

Workup

extractionThe mixture was extracted with CHCl3 (3×20 mL)
dry with materialThe combined organic layers was dried over MgSO4
concentrationconcentrated in vacuo
customto give a yellow oil

Sources & evidence

ORD record: ord-3bad6df07c9d4b5dab3a309ef15a4bfe
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196104B2

Reaction notes

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