Ethanol → 1-(6-Chloro-4-(3,4-methylenedioxybenzyl)aminoquinazolin-2-yl)piperidine-4-carboxylic acid

HRID 2392897Notes

Reaction equation

HRID 2392897 reaction equation
C(O)C.[OH-].[Na+].C([O:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([NH:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]4[O:35][CH2:36][O:37][C:31]=4[CH:30]=3)[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:38])[CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=[O:10])C>O>[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([NH:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]4[O:35][CH2:36][O:37][C:31]=4[CH:30]=3)[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:38])[CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)([OH:10])=[O:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 211838922-(4-Ethoxycarbonylpiperidino)-4-(3,4-methylenedioxy-benzyl)amino-6-chloroquinazoline

Product 1

HCID 53114861-(6-Chloro-4-(3,4-methylenedioxybenzyl)aminoquinazolin-2-yl)piperidine-4-carboxylic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of ethanol, 5 ml of water and 820 mg of sodium hydroxide were added to 1 g of 2-(4-ethoxycarbonylpiperidino)-4-(3,4-methylenedioxybenzyl)amino-6-chloroquinazoline. The obtained mixture was refluxed for 20 minutes, concentrated under a reduced pressure and neutralized with 1N hydrochloric acid. The crystals thus precipitated were recovered by filtration to give 920 mg of the title compound.

Workup

  1. temperatureThe obtained mixture was refluxed for 20 minutes
  2. concentrationconcentrated under a reduced pressure and neutralized with 1N hydrochloric acid
  3. customThe crystals thus precipitated
  4. filtrationwere recovered by filtration

Sources & evidence

ORD record
ord-1544c3cd36044d1e96e21612931c009d
Source dataset
uspto-grants-1998_09
Patent number
US05801180

Reaction notes

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