Allyl iodide → Quinolizidin-2-ylmethyl-1-allylindole-3-carboxylate

HRID 741563Notes

Reaction equation

HRID 741563 reaction equation
[CH2:1]1[CH:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH:2]1[CH2:11][O:12][C:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:14].[CH2:24](I)[CH:25]=[CH2:26]>>[CH2:1]1[CH:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH:2]1[CH2:11][O:12][C:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH2:26][CH:25]=[CH2:24])[CH:16]=1)=[O:14]

Participants

3

Reactant 2

HCID 11166Allyl iodideHCID 131719520Quinolizidin-2-ylmethylindole-3-carboxylate

Product 1

HCID 131719527Quinolizidin-2-ylmethyl-1-allylindole-3-carboxylate

Procedure

eq-Quinolizidin-2-ylmethylindole-3-carboxylate (E9b) was alkylated with allyl iodide using the method in Example 18. The product was chromatographed on silica gel eluting initially with ether, then with ethyl acetate, to afford the title compound (E19) as a colourless oil. This was converted to its hydrochloride salt mp 190°-192° C. (acetone)

Workup

  1. customThe product was chromatographed on silica gel eluting initially with ether

Sources & evidence

ORD record
ord-578c3311a7584e42b37f73ef5aea75c4
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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