1-Methylpiperazine → 2-Methyl-5-[2-(4-methyl-piperazin-1-yl)-ethyl]-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966526Notes

Reaction equation

[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21]OS(C)(=O)=O)[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>O1CCOCC1>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N:32]3[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]3)[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (424 mg, 1.1 mmol, Example 56, Step D) in dioxane (10 mL) was added 1-methylpiperazine (0.6 mL, 5.5 mmol). The mixture was stirred at 70° C. overnight and then partitioned between methylene chloride and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a solid residue, which was recrystallized from ethyl acetate to give 191 mg (45%) of the desired product as a white solid: mp 167-168° C.; MS(APCI+): m/z 392.3 (MH+); Anal. Calcd for C24H29N3O2.0.5H2O: C, 71.97; H, 7.55; N, 10.49. Found: C, 72.35; H, 7.54; N, 10.12.

Workup

custompartitioned between methylene chloride and water
washThe organic phase was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customto give a solid residue, which
customwas recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-7f54fb7d9d3a45908df322ae218cb249
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951848B2

Reaction notes

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