1-Methylpiperazine → Piperazine, 1-[2-bromo-5-(trifluoromethyl)phenyl]-4-methyl-

HRID 1473347Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1F>>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

Reactant 2

HCID 531671-Methylpiperazine

HCID 1424144-Bromo-3-fluorobenzotrifluoride

Product 1

HCID 86687472Piperazine, 1-[2-bromo-5-(trifluoromethyl)phenyl]-4-methyl-

Conditions

Temperature: 180 °C

Procedure

A microwave vial was charged with 1-methylpiperazine (1.371 ml, 12.35 mmol) and 4-bromo-3-fluorobenzotrifluoride (1.000 ml, 4.12 mmol), and was heated under microwave irradiation at 180° C. for 90 minutes. The reaction was concentrated under a vacuum, and the solids were then filtered and washed with DCM (the solids contained minor amounts of product but were disposed of). The filtrate was then concentrated under a vacuum to yield 1-(2-bromo-5-(trifluoromethyl)phenyl)-4-methylpiperazine. The material was carried forward without further purification. m/z (ESI) 323.0 (M+H)+.

Workup

concentrationThe reaction was concentrated under a vacuum
filtrationthe solids were then filtered
washwashed with DCM (the solids
concentrationThe filtrate was then concentrated under a vacuum

Sources & evidence

ORD record: ord-ae73dd8efade4d2e897a6ae0a7f9723a
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012443B2

Reaction notes

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