Ammonium Chloride → HCID 69122585, compound

HRID 2064090Notes

Reaction equation

HRID 2064090 reaction equation
[ClH:1].[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:12]3[CH:13]=[C:14]([O:17][C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:16][C:11]=3[NH:10][C:9]2=[O:22])[CH2:4][CH2:3]1.[O:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+]>C(N(CC)CC)C.ClCCCl>[ClH:1].[O:23]1[CH2:28][CH2:27][CH:26]([N:2]2[CH2:7][CH2:6][CH:5]([N:8]3[C:12]4[CH:13]=[C:14]([O:17][C:18]([F:19])([F:21])[F:20])[CH:15]=[CH:16][C:11]=4[NH:10][C:9]3=[O:22])[CH2:4][CH2:3]2)[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 57423926HCID 57423926, compound

Product 1

HCID 69122585HCID 69122585, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-(4-Piperidinyl)-6-[(trifluoromethyl)oxy]-1,3-dihydro-2H-benzimidazol-2-one hydrochloride D32 (0.6 g) 1,2-dichloroethane (50 mL) and triethylamine (10 mL), tetrahydro-4H-pyran-4-one (1.2 g), sodium triacetoxyborohydride (1.3 g) was stirred at room temperature over night. The mixture was poured into dilute ammonium chloride solution and extracted with dichloromethane. The organic phase was separated, washed with brine and dried with hydromatrix. The solvent was removed and the residue was chromatographed on silica gel eluted with dichloromethane/2M ammonia in methanol 0-10%. The resulting product was dissolved in a mixture of methanol and dichloromethane, treated with 1M hydrogen chloride in ether and the solvent was removed. Recrystallisation from methanol gave the title compound as a white solid (0.28 g).

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated
  3. washwashed with brine
  4. customdried with hydromatrix
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel
  7. washeluted with dichloromethane/2M ammonia in methanol 0-10%
  8. dissolutionThe resulting product was dissolved in a mixture of methanol and dichloromethane
  9. additiontreated with 1M hydrogen chloride in ether
  10. customthe solvent was removed
  11. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-2bdcc80a58d8478c9c7ebcd5f57223b6
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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