Cyclohexene → 3-Amino-2-(Boc-piperazinyl)pyridine

HRID 1484018Notes

Reaction equation

[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH:11]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.C1CCCCC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[C:5]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH:11]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

3-Nitro-2-(Boc-piperazine)pyridine 6 (1.765 g, 5.72 mmol) was dissolved in methanol (15 mL) at room temperature. Then Pd(OH)2 (1.234 g) and cyclohexene (2.0 mL, 19.52 mmol) were added. The resulting mixture was heated at 70° C. for 2 h. The mixture was concentrated to remove the solvent. DCM was added and then it was filtered through a pad of silica gel, washed with DCM and 10% MeOH/DCM. The collected solution was concentrated and dried under high vacuum to afford a slight pink solid as the product (1.384 g, 87% yield). 1H-NMR (CDCl3): 7.794 (dd, J=5.0 Hz and 1.5 Hz, 1H, Ar—H), 6.956 (dd, J=7.5 Hz and 1.5 Hz, 1H, Ar—H), 6.854 (dd, J=7.5 Hz and 5.0 Hz, 1H, Ar—H), 3.783 (br, 2H, NH2), 3.571 (t, J=4.5-5.0 Hz, 4H, 2 CH2), 3.059 (t, J=4.5-5.0 Hz, 4H, 2 CH2), 1.482 (s, 9H, 3 CH3). LC-MS: 279.2 (MH+). (ref. Romero D. L. et al. J. Med. Chem. 37, 999-1014, 1994.)

Workup

concentrationThe mixture was concentrated
customto remove the solvent
additionDCM was added
filtrationit was filtered through a pad of silica gel
washwashed with DCM and 10% MeOH/DCM
concentrationThe collected solution was concentrated
customdried under high vacuum

Sources & evidence

ORD record: ord-83e52d872dc84d028b077e709377689d
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09421204B2

Reaction notes

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