Hydrogen Bromide → HCID 9822606, compound

HRID 651384Notes

Reaction equation

HRID 651384 reaction equation
C[O:2][C:3]1[CH:30]=[CH:29][C:6]2[N:7]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)[CH2:15][CH2:14]3)[C:8](=[O:10])[NH:9][C:5]=2[CH:4]=1.Br>O>[OH:2][C:3]1[CH:30]=[CH:29][C:6]2[N:7]([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)[CH2:17][CH2:18]3)[C:8](=[O:10])[NH:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 21708345HCID 21708345, compound

Product 1

HCID 9822606HCID 9822606, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-methoxy-1-{2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethyl}-1,3-dihydrobenzimidazol-2-one (0.6 g; 1.4 mmol) and 48% HBr (30 ml) was refluxed for 1 hour. The reaction was then cooled and water was added (30 ml). The precipitated solid was collected and recrystallized from 95% EtOH to give the title compound as a white solid 0.4 g; m.p. 275° C. (as hydrobromide salt, from 95% ethanol). 1H-NMR (DMSO; 200 MHz): 10.82 (1H, s); 9.6, (1H, b); 9.11(1H, s); 7.47 (1H, m); 7.2-7.4 (2H, ov); 7.16 (1H, d); 7.03 (1H, d); 6.4-6.6 (2H, ov); 4.17 (2H, t); 4.03 (2H, d); 3.82 (2H, d); 3.51 (2H, b); 2.9-3.5 (4H, ov).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureThe reaction was then cooled
  3. customThe precipitated solid was collected
  4. customrecrystallized from 95% EtOH

Sources & evidence

ORD record
ord-5df6ba7a69ab49868de5640b9cad0887
Source dataset
uspto-grants-2001_08
Patent number
US06281218B1

Reaction notes

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