3-(4-Methyl-1-piperazine)propan-1-ol → 4-Chloro-6-cyano-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline

HRID 2222410Notes

Reaction equation

HRID 2222410 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.ClC1C2C(=CC(O)=C(C#N)C=2)[N:27]=[CH:26]C=1.OCCCN1CCN(C)CC1>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][N:27]([CH3:26])[CH2:20][CH2:19]3)=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 792083-(4-Methyl-1-piperazine)propan-1-olHCID 597122344-Chloro-6-cyano-7-(3-(pyrrolidin-1-yl)propoxy)quinolineHCID 1355837304-Chloro-6-cyano-7-hydroxyquinoline

Product 1

HCID 597122334-Chloro-6-cyano-7-(3-(4-methylpiperazin-1-yl)propoxy)quinolineYield 90%

Procedure

Using an analogous procedure to that described for the preparation of 4-chloro-6-cyano-7-(3-(pyrrolidin-1-yl)propoxy)quinoline, (starting material in Example 11), 4-chloro-6-cyano-7-hydroxyquinoline (8.2 g, 40 mmol), (prepared as described for the starting material in Example 1), was reacted with 1-(3-hydroxypropyl)-4-methylpiperazine (7.6 g, 48 mmol) to give 4-chloro-6-cyano-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline (12.4 g, 90%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-a3e3f372decf40c38f9add0eeb3755a3
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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