Hydrogen Bromide → 4-Methyl-3'-nitro-6'-piperazin-1-yl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl dihydrobromide

HRID 646939Notes

Reaction equation

C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:22]=[C:21]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[C:20]([N+:30]([O-:32])=[O:31])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[BrH:33].CCOCC>CC(O)=O>[BrH:33].[BrH:33].[CH3:29][CH:26]1[CH2:27][CH2:28][N:23]([C:21]2[C:20]([N+:30]([O-:32])=[O:31])=[CH:19][CH:18]=[C:17]([N:14]3[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]3)[N:22]=2)[CH2:24][CH2:25]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 4-(4-methyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl)-piperazine-1-carboxylic acid benzyl ester (as prepared in the previous step, 3.2 g, 7.3 mmol) in HOAc (50 mL) was treated with 30% HBr in HOAc (7.3 mL, 1 mL/mmol benzyl ester) and heated to 60° C. for 1 h. The reaction was cooled to room temperature and allowed to stir for 5 h, after which time Et2O was added to the reaction while stirring. The bright yellow precipitate was filtered and washed with Et2O to afford the title compound (2.6 g, 77%). 1H-NMR (CD3OD; 400 MHz): δ 8.44 (d, 1H, J=9.6 Hz), 6.95 (d, 1H, J=9.6 Hz), 4.13 (app t, 4H, J=5.2 Hz), 3.87-3.79 (m, 2H), 3.71-3.60 (m, 2H), 3.42 (app t, 4H, J=5.2 Hz), 2.09-2.00 (m, 2H), 1.99-1.88 (m, 1H), 1.69-1.55 (m, 2H), 1.09 (d, 3H, J=6.8 Hz). LC-MS (ESI, m/z): Calcd. for C15H23N5O2, 306.2 (M+H), found 306.1.

Workup

temperatureThe reaction was cooled to room temperature
stirringwhile stirring
filtrationThe bright yellow precipitate was filtered
washwashed with Et2O

Sources & evidence

ORD record: ord-41229446f00144ccbb9d701ca2f33a55
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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