Indole → 1-(5-Chloropentyl)-1H-indole

HRID 1832225Notes

Reaction equation

HRID 1832225 reaction equation
ClC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.N1C2C(=CC=CC=2)C=C1.BrCCCCC[Cl:32]>>[Cl:32][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

4

Reactant 3

HCID 798IndoleHCID 960701-Bromo-5-chloropentaneHCID 123407591-(6-Chlorohexyl)-1H-indole

Product 1

HCID 123407581-(5-Chloropentyl)-1H-indoleYield 80%

Procedure

According to the procedure used for the synthesis of 1-(6-chlorohexyl)-1H-indole, 1-H-indole (0.585 g, 5.00 mmol) and 1-bromo-5-chloropentane (0.928 g, 5.00 mmol) gave the desired product (0.890 g, 80%). 1H NMR (CDCl3) δ 7.76–7.51 (m, 1H), 7.44–6.96 (m, 4H), 6.60–6.38 (m, 1H), 4.11 (t, 2H, J=6.8 Hz), 3.47 (t, 2H, J=6.4 Hz), 1.97–1.79 (m, 2H), 1.79–1.61 (m, 2H), 1.58–1.32 (m, 2H).

Sources & evidence

ORD record
ord-3fdec60eccdf4d03a5541cc2077c7025
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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