Potassium Carbonate → HCID 69321501, compound

HRID 2217310Notes

Reaction equation

HRID 2217310 reaction equation
O.[ClH:2].Cl.Cl.Cl.[NH2:6][CH:7]([CH:38]([CH3:40])[CH3:39])[CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[N:20]([CH2:21][C:22]3[C:31]([O:32]C)=[CH:30][C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[N:23]=3)[C:19]3[CH:34]=[CH:35][CH:36]=[CH:37][C:18]=3[N:17]=2)[CH2:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+].BrB(Br)Br.[NH4+].[OH-]>ClCCl>[OH2:32].[ClH:2].[ClH:2].[ClH:2].[ClH:2].[NH2:6][CH:7]([CH:38]([CH3:40])[CH3:39])[CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[N:20]([CH2:21][C:22]3[C:31]([OH:32])=[CH:30][C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[N:23]=3)[C:19]3[CH:34]=[CH:35][CH:36]=[CH:37][C:18]=3[N:17]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 22037010HCID 22037010, compound

Product 1

HCID 69321501HCID 69321501, compoundYield 146.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(±)-N-[1-(2-amino-3-methylbutyl)-4-piperidinyl]-1-[(5,6,7,8-tetrahydro-3-methoxy-2-quinolinyl)methyl]-1H-benzimidazol-2-amine tetrahydrochloride monohydrate (0.00218 mol) was basified with K2CO3 10%. The mixture was extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated, to give A′. A mixture of A′ in dichloromethane (50 ml) was cooled to 0° C. A solution of tribromoborane in dichloromethane (0.01526 mol) was added dropwise. The mixture was stirred at room temperature overnight, poured out on ice, basified with a concentrated NH4OH solution, decanted and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (1.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 90/10/0.5; 20-45 μm). The desired fractions were collected and the solvent was evaporated. The residue was converted into the hydrochloric acid salt (1:4) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 0.5 g (37%) of (±)-N-[1-(2-amino-3-methylbutyl)-4-piperidinyl]-1-[(5,6,7,8-tetrahydro-3-hydroxy-2-quinolinyl)methyl]-1H-benzimidazol-2-amine tetrahydro-chloride monohydrate; mp. 240° C. (comp. 63).

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customto give A′
  7. additionpoured out on ice
  8. customdecanted
  9. extractionextracted with CH2Cl2
  10. customThe organic layer was separated
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customthe solvent was evaporated
  14. customThe residue (1.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 90/10/0.5; 20-45 μm)
  15. customThe desired fractions were collected
  16. customthe solvent was evaporated
  17. filtrationThe precipitate was filtered off
  18. customdried

Sources & evidence

ORD record
ord-fd7ed0a3c87f418796d52a300989e565
Source dataset
uspto-grants-2008_08
Patent number
US07407969B2

Reaction notes

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