Acetyl chloride → 3-[4-(4-p-Methoxyphenylpiperazino)butyl]-5-acetamidoindole, hydrochloride

HRID 36953

Reaction equation

HRID 36953 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([NH2:28])[CH:26]=4)[NH:21][CH:20]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[N+](C1C=C2C(=CC=1)NC=C2)([O-])=O.[C:41]([Cl:44])(=[O:43])[CH3:42]>C1COCC1>[ClH:44].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([NH:28][C:41](=[O:43])[CH3:42])[CH:26]=4)[NH:21][CH:20]=3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 225235-NitroindoleHCID 199364623-[4-(4-p-Methoxyphenylpiperazino)butyl]-5-aminoindole

Product 1

HCID 1317190083-[4-(4-p-Methoxyphenylpiperazino)butyl]-5-acetamidoindole, hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.5 g of 3-[4-(4-p-methoxyphenylpiperazino)butyl]-5-aminoindole ["D"; obtainable by reduction of the corresponding 5-nitroindole] in 35 ml of THF is treated with a solution of 0.9 g of acetyl chloride in 10 ml of THF, and the mixture is stirred for 2 hours at 50°, evaporated and worked up in a conventional manner. 3-[4-(4-p-Methoxyphenylpiperazino)butyl]-5-acetamidoindole, hydrochloride, m.p. 240° (dec.) is obtained.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-f03189a9faa146608c9b39960fa1611d
Source dataset
uspto-grants-1995_05
Patent number
US05418237

Linked notes

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