Piperidine → 2-Methyl-5-(2-piperidin-1-yl-ethyl)-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966528Notes

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.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]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:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]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: 80 °C

Procedure

To a solution of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (450 mg, 1.16 mmol, Example 56, Step D) in dioxane (10 mL) was added piperidine (1.1 mL, 11.6 mmol). The mixture was stirred at 80° C. for 2 hours 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 and diethyl ether to give 275 mg (63%) of the desired product as a white solid: mp 159-161° C.; MS(APCI+): m/z 377.1 (MH+); Anal. Calcd for C24H28N2O2.1.04H2O: C, 72.93; H, 7.67; N, 7.09. Found: C, 72.54; H, 7.31; N, 7.04.

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 and diethyl ether

Sources & evidence

ORD record: ord-cf9764e1b1f841eeac51cbfa962e71f3
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951848B2

Reaction notes

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