6-(3-Chloropropoxy)-3,4-dihydroquinolin-2(1H)-one → 6-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-1H-quinolin-2-one hydrochloride

HRID 1801644Notes

Reaction equation

HRID 1801644 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[NH:26][C:25](=[O:30])[CH2:24][CH2:23]5)[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2.[Cl:31]CCCOC1C=C2C(=CC=1)NC(=O)CC2.CO.Cl>CO>[ClH:31].[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[NH:26][C:25](=[O:30])[CH2:24][CH2:23]5)[CH2:14][CH2:15]3)=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 110428286-(3-Chloropropoxy)-3,4-dihydroquinolin-2(1H)-oneHCID 119788176-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-1H-quinolin-2-oneHCID 21893726Hydrochloride methanol

Product 1

HCID 668846016-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-1H-quinolin-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By a similar method as in Example 1, 6-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-1H-quinolin-2-one was prepared from 6-(3-chloropropoxy)-3,4-dihydro-1H-quinolin-2-one, and after it was made into a methanol solution, 0.5N hydrochloric acid methanol solution was added thereto, precipitated crystals were separated by filtration, recrystallized from a mixed solvent of ethyl acetate-diethyl ether and thereby 6-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-1H-quinolin-2-one hydrochloride was obtained in the form of a white powder.

Workup

  1. additionwas added
  2. customprecipitated crystals
  3. customwere separated by filtration
  4. customrecrystallized from a mixed solvent of ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-4821b1d4897849bd9dbdce347dc5a8d4
Source dataset
uspto-grants-2013_01
Patent number
US08349840B2

Reaction notes

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