Potassium Hydroxide → 4-Piperidin-4-yl-7-(3-piperidin-1-yl-propoxy)-quinazoline
Reaction equation
[OH-].[K+].COC([C:7]1([C:20]2[C:29]3[C:24](=[CH:25][C:26](Cl)=[CH:27][CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)=O.[OH:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>O>[NH:10]1[CH2:9][CH2:8][CH:7]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:31][CH2:32][CH2:33][CH2:34][N:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:27][CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH2:12][CH2:11]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Solid KOH (112 mg, 2 mmol) was added to a mixture of 4-(7-chloro-quinazolin-4-yl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (3a; 82 mg, 0.2 mmol), prepared as described in Example 3, and 3-hydroxypropylpiperidine (0.25 mL). The mixture was stirred at 100° C. for 3 h. It was then cooled to rt and diluted with water. The mixture was extracted with DCM and the organic layer was drawn off and washed with water thrice, with brine once, then dried over anhydrous MgSO4, filtered and concentrated in vacuo. To this was added 3 ML of 3M HCl/MeOH and the mixture was stirred at rt for 2 h and then concentrated in vacuo to afford crude 4-piperidin-4-yl-7-(3-piperidin-1-yl-propoxy)-quinazoline.
Workup
- customprepared
- temperatureIt was then cooled to rt
- extractionThe mixture was extracted with DCM
- washwashed with water thrice, with brine once
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- additionTo this was added 3 ML of 3M HCl/MeOH
- stirringthe mixture was stirred at rt for 2 h
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c19e6b6136344674a5924edc1e90a2e8
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825244B2
Reaction notes
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