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

HRID 494976Notes

Reaction equation

O1[C:5]2([CH2:10][CH2:9][N:8]([CH2:11][CH2:12][C:13]3[CH:22]=[C:21]4[C:16]([CH2:17][CH2:18][CH2:19][N:20]4[CH3:23])=[CH:15][C:14]=3[O:24][CH3:25])[CH2:7][CH2:6]2)[O:4]CC1.C(=O)(O)[O-].[Na+]>Cl.O1CCCC1>[CH3:25][O:24][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:13]=1[CH2:12][CH2:11][N:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1)[N:20]([CH3:23])[CH2:19][CH2:18][CH2:17]2

Participants

Conditions

Temperature: 70 °C

Procedure

100 mg of 7-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1-methyl-1,2,3,4-tetrahydroquinoline was dissolved in 6 ml of 2 N hydrochloric acid-tetrahydrofuran (1:1). The reaction solution was stirred at 70° C. for 7 hours. The reaction solution was cooled to a room temperature. Thereafter, 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 87 mg of 1-(2-(6-methoxy-1-methyl-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-a3226ea612fd45beb0838c727a59ba15
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538123B2

Reaction notes

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