Hydrochloric Acid → HCID 19802564, compound

HRID 1645819Notes

Reaction equation

HRID 1645819 reaction equation
B.CSC.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:19](=O)[CH:20]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:21]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:23]=[CH:22]2)[CH2:15][CH2:14]1.Cl>C1COCC1>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH:20]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:21]2[CH:25]=[C:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:23]=[CH:22]2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 67749829HCID 67749829, compound

Product 1

HCID 19802564HCID 19802564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
90 °C

Procedure

2.0 M Borane-methylsulphide in THF (45 ml) was added over 45 mins to a solution of 1-(2-methoxyphenyl)-4-[1-oxo-2-phenyl-2-(4-phenyl-1H-imid azol-1-yl) ethyl]piperazine (4.0 g, 0.009 m, prepared in an analogous manner to the method of Example 5a) in dry THF (30 ml) at ambient temperature, and the mixture was then refluxed 24 hrs. The cooled mixture was treated with conc. HCl (25 ml) dropwise over 30 mins and the resulting white suspension was then heated at 90° C. for 4 hrs. After further standing 48 hrs the mixture was filtered. The white solid was washed with 6N HCl and dried, then recrystallised from ethanol to yield the title compound as the trihydrochloride (1.425 g), m.p. 233°-36° C.(d).

Workup

  1. temperaturethe mixture was then refluxed 24 hrs
  2. filtrationthe mixture was filtered
  3. washThe white solid was washed with 6N HCl
  4. customdried
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-9e20da64c0f04275995ee904a0cf9438
Source dataset
uspto-grants-1993_01
Patent number
US05177078

Reaction notes

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