1-Methylpiperazine → HCID 9968233, compound

HRID 985725Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8][CH:7]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[NH:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH2:24][CH2:23]1

Participants

Reactant 2

HCID 531671-Methylpiperazine

HCID 22507775HCID 22507775, compound

Product 1

HCID 9968233HCID 9968233, compound

Conditions

Temperature: 80 °C

Procedure

The mixture of (2-(4-(3-chloropropoxy)phenyl)indole (1 mmol, 285 mg) and 4-methylpiperazine (2 mL) was heated at 80° C. for 5 h. After concentration, the residue was purified by column chromatography (MeOH/CH2Cl2) afforded the title compound (285 mg): 1H NMR (CDCl3, 400 MHz) δ 8.26 (s, 1H), 7.53 (m, 3H), 7.32 (bd, 1H, J=8.1 Hz), 7.1 (td, 1H, J=1.1, 7.0 Hz), 7.05 (td, 1H, J=1.1, 7.0 Hz), 6.90 (m, 2H), 6.64 (m, 1H), 3.99 (t, 2H, J=6.3 Hz), 2.48 (m, 10H, J=6.4 Hz), 2.25 (s, 3H), 1.93 (quintet, 2H, J=6.3 Hz); EIMS m/z 350 (M+H+).

Workup

concentrationAfter concentration
customthe residue was purified by column chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-ed4c590d39a745b199c7a92a95cb2565
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872834B2

Reaction notes

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