Hydrochloric Acid → HCID 15016120, compound

HRID 2226110Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:11][CH2:10]1.C([Li])CCC.[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1.Cl>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH:16]([CH2:33][C:32]2[CH:35]=[CH:36][C:29]([F:28])=[CH:30][CH:31]=2)[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)[CH2:13][CH2:14]1

Participants

Conditions

Temperature: -78 °C

Procedure

1-(2-Methoxyphenyl)-4-[2-(4-pyridyl)ethyl]piperazine (5.94 g, 20 mmol) was dissolved in anhydrous THF (70 ml) and the solution cooled to about -78° C., n-Butyllithium (1.6M solution in hexane, 18 ml) was added in portions, then the mixture was stirred for 1 hour, at below -70° C. The anion was quenched with p-fluorobenzylbromide (3.18 g, 16.8 mmol) in THF (3 ml and the mixture was warmed to room temperature when water (50 ml) was added. The organic component was extracted by dichloromethane, then washed with brine, dried using sodium sulphate and concentrated in vacuo. The resulting oil was purified by column chromatography using methanol:chloroform (0:100-5:95 gradient), affording the pure product. Addition of ethanolic HCl to the oil gave the title compound as the trihydrochloride 1.5 hydrate (1.25 g), m.p. 173°-175° C.

Workup

additionwas added
extractionThe organic component was extracted by dichloromethane
washwashed with brine
customdried
concentrationconcentrated in vacuo
customThe resulting oil was purified by column chromatography
customaffording the pure product

Sources & evidence

ORD record: ord-7ff2b03bda414fd1a1840691bbd6524d
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05346896

Reaction notes

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