Hydrochloric Acid → 1-[2-Fluoro-3-(trifluoromethyl)phenyl]-4-(2-methoxyethyl)piperazine

HRID 1878951Notes

Reaction equation

HRID 1878951 reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][O:27][CH3:28].Cl>C(#N)C>[F:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[N:12]1[CH2:13][CH2:14][N:15]([CH2:25][CH2:26][O:27][CH3:28])[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 574480411-(2-Fluoro-3-(trifluoromethyl)phenyl)piperazine

Product 1

HCID 593896381-[2-Fluoro-3-(trifluoromethyl)phenyl]-4-(2-methoxyethyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 1: 1-[2-fluoro-3-(trifluoro-methyl)phenyl]piperazine (0.5 g, 2.0 mmol), acetonitrile (25 ml), potassium carbonate (0.42 g, 3.0 mmol) and 1-bromo-2-methoxyethane (0.189 ml, 2.0 mmol). Yield: 0.26 g (42%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 170-171° C. MS m/z (relative intensity, 70 eV) 306 (M+, 9), 262 (13), 261 (bp), 218 (23), 190 (23).

Workup

  1. customPreparation
  2. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-3139b598cd2c4759b697b8c2fa507976
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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