Pyridine → HCID 178515489, compound

HRID 743722Notes

Reaction equation

C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([OH:32])([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[N:26]=[C:25]([O:30]C)[CH:24]=[CH:23]4)=[CH:16][CH:15]=2)[CH2:9]1)C1C=CC=CC=1.BrC1C=CC(C2C=C3C(=CC=2)N=C(OC)C=C3)=CC=1.N1C=CC=CC=1.C[Si](I)(C)C>CO.C(Cl)(Cl)Cl>[OH:32][C:10]1([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[N:26]=[C:25]([OH:30])[CH:24]=[CH:23]4)=[CH:18][CH:19]=2)[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1

Participants

Conditions

Temperature: 55 °C

Procedure

By the method described in Preparation 7, 1-benzyl-3-hydroxy-3-(4-(2-methoxyquinolin-6-yl)phenyl)piperidine is prepared from 6-(4-bromophenyl)-2-methoxyquinoline. This material (0.20 g, 0.471 mmol) is placed in a sealed tube under nitrogen with chloroform (5 mL), pyridine (0.02 ml, 0.075 mmol). and trimethylsilyliodide (0.107 ml, 0.754 mmol). The mixture is heated slowly to 55° C. in an oil bath for fifteen hours with stirring. The sealed tube is cooled to 0° C., opened and the contents diluted with methanol (50 ml). The solution is concentrated to dryness and the crude residue is purified by flash column chromatography using 10% methanol in methylene chloride to yield of 1-benzyl-3-hydroxy-3-(4-(2-hydroxyquinolin-6-yl)phenyl)piperidine as a yellow solid (0.1 g, 51%). The debenzylation is carried out as in preparation 1 to yield 3-hydroxy-3-(4-(2-hydroxyquinolin-6-yl)-phenyl)-piperidine.

Workup

temperatureThe sealed tube is cooled to 0° C.
concentrationThe solution is concentrated to dryness
customthe crude residue is purified by flash column chromatography
customThe debenzylation is carried out as in preparation 1

Sources & evidence

ORD record: ord-27dfe8b3c0704f86b83d44827b9727b0
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556990

Reaction notes

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