Water → HCID 86758140, compound

HRID 2186338Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]#[CH:24])[CH2:18][C@@H:17]1[C:25]([O:27]CC#C)=[O:26].[OH-].[Na+].O>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]#[CH:24])[CH2:18][C@@H:17]1[C:25]([OH:27])=[O:26]

Participants

Conditions

Temperature: 70 °C

Procedure

0.3 g of (prop-2-ynyl) (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)piperidine-3-carboxylate in 3 cm3 of dioxane and 1.48 cm3 of N sodium hydroxide were heated, with stirring, at a temperature in the region of 70° C. for 17 hours. The reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C. 1.48 cm3 of normal aqueous hydrochloric acid were added to the solid residue obtained, followed by 10 cm3 of water. The solution obtained was extracted with 5 times 20 cm3 of dichloromethane. The organic extracts were combined and then concentrated under reduced pressure (5 kPa). 0.189 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)piperidine-3-carboxylic acid was obtained in the form of a foam with a white color.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C
addition1.48 cm3 of normal aqueous hydrochloric acid were added to the solid residue
customobtained
customThe solution obtained
extractionwas extracted with 5 times 20 cm3 of dichloromethane
concentrationconcentrated under reduced pressure (5 kPa)

Sources & evidence

ORD record: ord-c3dbb50a3b6f4eccb41af679a420e2fc
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403610B1

Reaction notes

Loading…