Sodium Hydroxide → HCID 23291093, compound

HRID 365307Notes

Reaction equation

HRID 365307 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[NH:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=2[CH:17]=1.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH2:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[OH-].[Na+]>C(Cl)(Cl)Cl>[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[NH:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=3[CH:17]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 43753132-(1-Piperazinylmethyl)quinolineHCID 23291091HCID 23291091, compound

Product 1

HCID 23291093HCID 23291093, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

A mixture consisting of 7-(3-chloropropoxy)-2,3,4,5-tetrahydro-1H-benzoazepin-2-one (0.304 g, 1.2 mmol) and 1-(2-quinolylmethyl)piperazine (1.091 g, 4.8 mmol) was stirred for 4 hours at a bath temperature of 150° C. under an argon gas stream. The reaction mixture was dissolved in chloroform. The thus-obtained solution was rendered basic with a dilute aqueous solution of sodium hydroxide, washed with water, and then dried over magnesium sulfate. After the resulting solution was purified by subjecting it to chromatography on a silica gel column (developer: chloroform/methanol=40/1), recrystallization was conducted from acetone. The title compound (0.270 g) was obtained as yellow prisms (yield: 50.6%).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customAfter the resulting solution was purified
  4. customon a silica gel column (developer: chloroform/methanol=40/1), recrystallization

Sources & evidence

ORD record
ord-dcbdf60b2c55426b8ef6c9a1bbc4115d
Source dataset
uspto-grants-2000_10
Patent number
US06127360

Reaction notes

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