Potassium Hydroxide → 2-[4-[3-(1-Piperidinyl)propoxy]phenyl]-1H-indole

HRID 985723Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:18](S(C)(=O)=O)[C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CO>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[NH:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of the product from Step F, Example 1 (41.4 mg, 0.10 mmol) in methanol (2.0 mL) was treated with potassium hydroxide (1.0 mL, 40% aq). The reaction was stirred at 40° C. for 48 hours and concentrated in vacuo. The residue was purified by silica gel chromatography (methanol:dichloromethane) to provide pure title compound (3.7 mg). MS (ESI) m/z 335 (MH+); 1H-NMR (CDCl3) δ 8.19 (bs, 1H), 7.48 (d, 2H), 7.27 (m, 2H), 7.07 (t, 1H), 7.00 (t, 1H), 6.86 (d, 2H), 6.61 (s, 1H), 3.96 (t, 2H), 2.5 (m, 6H), 1.4 (m, 8H).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (methanol:dichloromethane)

Sources & evidence

ORD record: ord-283d029c293845e596b86b6e7dac82db
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872834B2

Reaction notes

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