2-Methylpiperazine → 3-Methyl-1-[(5-nitro-1-benzofuran-7-yl)methyl]piperazine

HRID 1162057Notes

Reaction equation

HRID 1162057 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][CH:16]1[CH2:21][NH:20][CH2:19][CH2:18][NH:17]1>>[CH3:15][CH:16]1[NH:17][CH2:18][CH2:19][N:20]([CH2:2][C:3]2[C:11]3[O:10][CH:9]=[CH:8][C:7]=3[CH:6]=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=2)[CH2:21]1

Participants

3

Reactant 2

HCID 660572-MethylpiperazineHCID 534029717-(Bromomethyl)-5-nitrobenzofuran2×

Product 1

HCID 668932103-Methyl-1-[(5-nitro-1-benzofuran-7-yl)methyl]piperazineYield 95%

Procedure

The title compound was prepared according to the procedure of Example 112, Step 1, starting from 7-(bromomethyl)-5-nitro-1-benzofuran (120 mg, 70 mol %, 0.39 mmol; Intermediate 64) and 2-methylpiperazine (196 mg, 1.95 mmol). The crude product was purified by flash chromatography (eluent: 4% MeOH, 1% NEt3 in DCM). The title compound (102 mg, 87%) was obtained as a light yellow sticky oil. HPLC 99%, RT=1.60 min (System A; 5-60% MeCN over 3 min), 100%, RT=1.40 min (System B; 5-60% MeCN over 3 min). MS (ESI+) for C14H17N3O3 m/z 276 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by flash chromatography (eluent: 4% MeOH, 1% NEt3 in DCM)

Sources & evidence

ORD record
ord-94bfdf0ab8264c828fd51f5012a15411
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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