Acetic Acid → HCID 21193397, compound

HRID 443311Notes

Reaction equation

HRID 443311 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:14]([C:16]1[N:20]([CH2:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[CH:19]=[N:18][CH:17]=1)=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].[ClH:53]>ClCCCl.C(#N)C>[ClH:53].[C:1]1([N:7]2[CH2:8][CH2:9][CH:10]([NH:13][CH2:14][C:16]3[N:20]([CH2:21][C:22]4[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=4)[CH:19]=[N:18][CH:17]=3)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrileHCID 211933471-Phenylpiperidin-4-amine

Product 1

HCID 21193397HCID 21193397, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6342AcetonitrileSolvent

Procedure

1-Phenylpiperidin-4-ylamine (75 mg, 0.43 mmol) (from Example 123) and 4-(5-formylimidazol-1-ylmethyl)benzonitrile (99 mg, 0.47 mmol) were dissolved in 1,2-dichloroethane (2 mL) and acetic acid (49 μL, 0.86 mmol) was added. The mixture was stirred for 2 hrs at room temperature, then sodium triacetoxyborohydride (117 mg, 0.55 mmol) was added, then the reaction mixture was stirred at room temperature for 18 hrs. Sat. NaHCO3 (aq) (30 mL) was added, and the organic layer was extracted. The aqueous phase was extracted with dichloromethane (2×5 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with dichloromethane--5% methanol--0.5% NH4OH to give the product as a free base. This was lyophilized from HCl (aq)--acetonitrile to give the title compound as a white solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hrs
  2. extractionthe organic layer was extracted
  3. extractionThe aqueous phase was extracted with dichloromethane (2×5 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluting with dichloromethane--5% methanol--0.5% NH4OH
  9. customto give the product as a free base

Sources & evidence

ORD record
ord-39093cad1e5b43909357e9afccb8ed89
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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