Pyridine → 4-(3-Trifluoromethyl-benzyl)-piperazine-1-carbonyl chloride

HRID 550853Notes

Reaction equation

[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.[F:19][C:20]([F:35])([F:34])[C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[CH2:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>O1CCCC1>[F:35][C:20]([F:19])([F:34])[C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:2]([Cl:1])=[O:4])[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 25 °C

Procedure

A magnetically stirred mixture of triphosgene (365 mg, 1.23 mmol) in tetrahydrofuran (20 mL) under a nitrogen atmosphere was treated slowly with pyridine (485 mg, 6.15 mmol) via syringe. The resulting white suspension was then treated with a solution of 1-(3-Trifluoromethyl-benzyl) piperazine (1.0 g, 4.10 mmol) in tetrahydrofuran (10 mL) via addition funnel over 10 min. The reaction mixture was stirred at 25° C. overnight. At this time, the reaction was filtered to remove solids. The filtrate was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 60:40 hexanes/ethyl acetate afforded 4-(3-Trifluoromethyl-benzyl)-piperazine-1-carbonyl chloride (350 mg, 28%) as a clear oil. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

filtrationAt this time, the reaction was filtered
customto remove solids
concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record: ord-c3155bcea5e3487984b9722812f8915f
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947692B2

Reaction notes

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