Piperidine → 6-Methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-one

HRID 384826Notes

Reaction equation

HRID 384826 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16]Cl)[N:9]=[CH:8][NH:7][C:6]2=[O:18].[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[N:9]=[CH:8][NH:7][C:6]2=[O:18]

Participants

4

Reactant 3

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 1355897776-Methoxy-7-(3-chloropropoxy)quinazolin-4-one

Product 1

HCID 1354715536-Methoxy-7-(3-piperidinopropoxy)-3,4-dihydroquinazolin-4-oneYield 85%

Conditions

Temperature
50 °C

Procedure

In a 5 mL volume glass vessel equipped with a stirrer and a thermometer were placed 0.5 g (1.9 mmol) of 6-methoxy-7-(3-chloropropoxy)quinazolin-4-one prepared by procedures similar to those of Reference Example V-1, 0.81 g (9.5 mmol) of piperidine, and 4.8 mL (19 mmol) of aqueous sodium hydroxide solution (4.0 mol/L). The resulting mixture was stirred at 50° C. for 5 hours. After the reaction was complete, the reaction mixture was analyzed by high performance liquid chromatography (absolute quantitative analysis). There was produced 0.51 g (reaction yield: 85%) of 6-methoxy-7-(3-piperidinopropoxy)-quinazolin-4-one.

Workup

  1. customIn a 5 mL volume glass vessel equipped with a stirrer

Sources & evidence

ORD record
ord-6e09e49e33fc4b1dac448e90d24f859c
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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