Hydrogen Bromide → 1-[2-(2,2,2-Trifluoroethoxy)-4-hydroxyphenyl]piperazine hydrobromide

HRID 342553Notes

Reaction equation

HRID 342553 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11]C)[CH:8]=[CH:7][C:6]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[BrH:21]>>[BrH:21].[F:20][C:2]([F:1])([F:19])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[N:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 701982161-[2-(2,2,2-Trifluoroethoxy)-4-methoxyphenyl]piperazine

Product 1

HCID 702042411-[2-(2,2,2-Trifluoroethoxy)-4-hydroxyphenyl]piperazine hydrobromide

Conditions

Temperature
0 °C

Procedure

A mixture of 1-[2-(2,2,2-trifluoroethoxy)-4-methoxyphenyl]piperazine (1.87 g, 6.4 mmol) and 48% aqueous hydrobromic acid (5 mL) was heated 17 hours at reflux. The reaction mixture was allowed lo cool and then concentrated in vacuo. The residue was dissolved in ethanol (10 mL) at approximately 55° C. and the solution was cooled to 0° C. The solids were collected, washed with cold ethanol (3×10 mL) and dried in vacuo at approximately 80° C. to give 1-[2-(2,2,2-trifluoroethoxy)-4-hydroxyphenyl]piperazine hydrobromide, m.p. 190-194. Anal.: Calcd. for C12H14F3N2O2.(HBr)0.5. H2O: C, 43.00; H, 5.27; N, 8.37%; Found: C, 43.41; H, 4.97; N, 8.36%.

Workup

  1. temperaturewas heated 17 hours
  2. temperatureat reflux
  3. temperaturecool
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethanol (10 mL) at approximately 55° C.
  6. customThe solids were collected
  7. washwashed with cold ethanol (3×10 mL)
  8. customdried in vacuo at approximately 80° C.

Sources & evidence

ORD record
ord-8ddf585c0cb04f638be63fa2f83b5897
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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