Hydrogen Bromide → HCID 178419328, compound

HRID 271676Notes

Reaction equation

HRID 271676 reaction equation
[N:1]1([CH2:6][C:7]2[NH:11][C:10]3[CH:12]=[CH:13][C:14](N)=[CH:15][C:9]=3[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.N([O-])=O.[Na+].[BrH:22]>>[Br:22][C:14]1[CH:13]=[CH:12][C:10]2[NH:11][C:7]([CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:8][C:9]=2[CH:15]=1

Participants

5

Reactant 4

HCID 260Hydrogen Bromide2×HCID 962WaterHCID 23668193Sodium NitriteHCID 178507352HCID 178507352, compound

Product 1

HCID 178419328HCID 178419328, compound

Conditions

Temperature
0 °C

Procedure

3.10 g (14.3 mmol) 2-pyrrolidin-1-ylmethyl-1H-benzimidazol-5-ylamine is suspended in 32.2 mL 48% hydrobromic acid and 32.2 mL water and the solution is cooled to 0° C. 2.5 M sodium nitrite solution (1.68 g in 9.7 mL water) is slowly added dropwise, so that the internal temperature does not exceed 5° C. The reaction is stirred for 10 min at 0° C. and then 3.50 g (24.37 mmol) CuBr in 11.3 mL 48% hydrobromic acid is added dropwise. The reaction is heated to 60° C. and stirred for one hour at this temperature. The solvent is eliminated i.vac. and the residue triturated with isopropanol. The precipitate is suction filtered and washed with isopropanol. The purification is carried out by column chromatography on silica gel (MeOH/NH3 9:1).

Workup

  1. customdoes not exceed 5° C
  2. temperatureThe reaction is heated to 60° C.
  3. stirringstirred for one hour at this temperature
  4. customand the residue triturated with isopropanol
  5. filtrationfiltered
  6. washwashed with isopropanol
  7. customThe purification

Sources & evidence

ORD record
ord-dc68a8da957548afb507713ef93c271b
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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