Sodium Bicarbonate → 1-(2-(1-Acetyl-6-methoxy-1,2,3,4-tetrahydroquinolin-7-yl)ethyl)piperidin-4-one

HRID 494972Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:26][CH3:27])=[C:11]([CH2:14][CH2:15][N:16]3[CH2:25][CH2:24][C:19]4(OCC[O:20]4)[CH2:18][CH2:17]3)[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+]>Cl.O1CCCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:26][CH3:27])=[C:11]([CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][C:19](=[O:20])[CH2:24][CH2:25]3)[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

162 mg of 1-acetyl-7-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4-tetrahydroquinoline was dissolved in 6 ml of 2 N hydrochloric acid-tetrahydrofuran (1:1), and the reaction solution was then stirred at 70° C. for 10 hours. The reaction solution was cooled to a room temperature, and a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure, so as to obtain 127 mg of 1-(2-(1-acetyl-6-methoxy-1,2,3,4-tetrahydroquinolin-7-yl)ethyl)piperidin-4-one. This compound was used in the following reaction without further purification.

Workup

temperatureThe reaction solution was cooled to a room temperature
extractionfollowed by extraction with methylene chloride
dry with materialThe extract was dried over magnesium sulfate
concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record: ord-8eb7e735a7c4486b86e7dcfe484f9738
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538123B2

Reaction notes

Loading…