Allyl bromide → HCID 11338659, compound

HRID 1840948Notes

Reaction equation

HRID 1840948 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([O:23]C)=[O:22])[CH2:12][CH2:11]2)=[CH:2]1.[H-].[Na+].[CH2:31](Br)[CH:32]=[CH2:33]>>[CH2:33]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][O:18][C:19]3[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=3[C:21]([OH:23])=[O:22])[CH2:14][CH2:15]2)=[CH:2]1)[CH:32]=[CH2:31]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 11440344methyl 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoate

Product 1

HCID 11338659HCID 11338659, compound

Procedure

This compound was prepared following the procedure described in Example 138 (part B) starting with 2.8 g (7.4 mmol) of methyl 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoate, 0.38 g (9.6 mmol) of NaH in 60% of mineral oil and 0.77 mL (8.9 mmol) of allyl bromide. The crude mixture was hydrolised following the procedure described in Example 138 (part C) and purified by chromatography over silica gel affording 0.62 g (23% of yield) of the desired product.

Workup

  1. customThis compound was prepared
  2. custompurified by chromatography over silica gel affording 0.62 g (23% of yield) of the desired product

Sources & evidence

ORD record
ord-dd9eb1f3902b49ffaf6e889eecca9190
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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