Sodium Hydroxide → 5-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole
Reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]#[C:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][CH:26]([CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH2:25][CH2:24]4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[CH2:29]([CH:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][C:20]#[C:19][C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[NH:10][CH:11]=[CH:12]3)[CH2:24][CH2:25]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1Participants
4
Procedure
A mixture of 1-benzenesulfonyl-5-[4-(4-benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole (1.49 g, 3.1 mmol) is stirred in EtOH (200 mL) and 50% NaOH (1 mL) at room temperature for 3 days. Most of the EtOH is evaporated and the residue diluted with water (200 mL). The precipitate is filtered off and washed copiously with water. The precipitate is recrystallized from hot EtOH to give the title compound as an off-white solid (854 mg): mp 165-166° C.