1,4'-Bipiperidine → 3-[1,4']Bipiperidinyl-1'-ylmethyl-2-phenyl-quinoline-4-carboxylic Acid Methyl Ester

HRID 1166273Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]=1[CH2:21]Br)=[O:4].[N:23]1([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(N(C(C)C)C(C)C)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]=1[CH2:21][N:32]1[CH2:33][CH2:34][CH:29]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:30][CH2:31]1)=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

5 g (14 mmol) of 3-bromomethyl-2-phenyl-quinoline-4-carboxylic acid methyl ester (compound of Description 2), 2.9 g, (15.4 mmol) of 90% [1,4′]Bipiperidinyl (Aldrich), 2.7 ml (15.4 mmol) of ethyl-diisopropyl-amine were dissolved in 100 ml of dry THF and the mixture was stirred for one night at 50° C. The solvent was concentrated, the residue was dissolved in CH2Cl2, washed with water, and the organic phase was dried over MgSO4. After concentration of the solvent, the residue was purified by flash chromatography over 160 g of silicagel (eluting with CH2Cl2/MeOH/NH4OH:95/5/0.5) affording 3.5 g (yield 56%) of the title compound as a white solid.

Workup

concentrationThe solvent was concentrated
dissolutionthe residue was dissolved in CH2Cl2
washwashed with water
dry with materialthe organic phase was dried over MgSO4
customAfter concentration of the solvent, the residue was purified by flash chromatography over 160 g of silicagel (eluting with CH2Cl2/MeOH/NH4OH:95/5/0.5)

Sources & evidence

ORD record: ord-24c88c5e2f9c48b6b9c7b44b15e597e6
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613770B1

Reaction notes

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