2,5-Dimethylpiperazine, trans- → trans-2,5-Dimethyl-1-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine

HRID 1162064Notes

Reaction equation

Br[CH2:2][C:3]1[C:11]2[O:10][CH:9]=[CH:8][C:7]=2[CH:6]=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[CH3:15][C@H:16]1[CH2:21][NH:20][C@H:19]([CH3:22])[CH2:18][NH:17]1>>[CH3:15][C@H:16]1[CH2:21][NH:20][C@H:19]([CH3:22])[CH2:18][N:17]1[CH2:2][C:3]1[C:11]2[O:10][CH:9]=[CH:8][C:7]=2[CH:6]=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

Reactant 2

HCID 2206722,5-Dimethylpiperazine, trans-

HCID 534029717-(Bromomethyl)-5-nitrobenzofuran

Product 1

HCID 66893199trans-2,5-Dimethyl-1-[(5-nitro-1-benzofuran-7-yl)methyl]piperazineYield 63.4%

Procedure

The title compound was prepared according to the procedure of Example 112, Step 1, starting from 7-(bromomethyl)-5-nitro-1-benzofuran (0.16 g, 0.6 mmol) and trans-2,5-dimethylpiperazine (0.36 g, 3.1 mmol). This afforded the title product (0.11 g, 60%) as a light yellow solid. HPLC 98% RT=1.26 min (System A; 10-97% MeCN over 3 min). 1H NMR (400 MHz, CDCl3) δ ppm 0.93 (d, J=6.3 Hz, 3H) 1.17 (d, J=6.0 Hz, 3H) 1.48 (br s, 1H) 1.79 (dd, J=11.0, 10.3 Hz, 1H) 2.29-2.41 (m, 1H) 2.63-2.75 (m, 2H) 2.80-2.89 (m, 1H) 2.93 (dd, J=12.0, 3.3 Hz, 1H) 3.61 (d, J=14.6 Hz, 1H) 4.28 (d, J=14.3 Hz, 1H) 6.91 (d, J=2.3 Hz, 1H) 7.76 (d, J=2.3 Hz, 1H) 8.29 (d, J=2.3 Hz, 1H) 8.41 (d, J=2.3 Hz, 1H). MS (ESI+) m/z 290.1 (M+H)+.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-b46b76ad56f84cf28afc45a59efcf1bb
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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