Sodium Hydroxide → 5-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

HRID 1279385Notes

Reaction equation

HRID 1279385 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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 184279561-Benzenesulfonyl-5-[4-(4-benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

Product 1

HCID 106410735-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indoleYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. customMost of the EtOH is evaporated
  2. additionthe residue diluted with water (200 mL)
  3. filtrationThe precipitate is filtered off
  4. washwashed copiously with water
  5. customThe precipitate is recrystallized from hot EtOH

Sources & evidence

ORD record
ord-108c3faaac79487d9efe13dbf5711002
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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