1-Methyl-4-piperidone → HCID 72194407, compound

HRID 1486825Notes

Reaction equation

HRID 1486825 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)[C:12]3[C:31]([Cl:35])=[CH:32][CH:33]=[N:34][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:36][N:37]1[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:20]=[CH:21][C:22]([N:25]5[CH2:30][CH2:29][N:28]([CH:40]6[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]6)[CH2:27][CH2:26]5)=[CH:23][CH:24]=4)=[CH:16][CH:17]=3)[C:12]3[C:31]([Cl:35])=[CH:32][CH:33]=[N:34][C:11]2=3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 740491-Methyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydrideHCID 89893997HCID 89893997, compound

Product 1

HCID 72194407HCID 72194407, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

Under an inert atmosphere 9-benzenesulfonyl-4-chloro-6-(4-(piperazin-1-yl)phenyl)-9H-pyrido[2,3-b]indole (30 mg, 0.0596 mmol) was dissolved in anhydrous DCM (1.2 mL, c=0.05M). N-methyl-4-piperidone (22 μL, 3 eq) was added, followed by the addition of two drops of glacial acetic acid. The mixture was stirred for 1 h15 at r.t. and then cooled to 0° C. Sodium triacetoxyborohydride (38 mg, 3eq) was added in portions and the resultant mixture was allowed to warm to room temperature, and then stirred 22 h. The reaction mixture was then quenched with water and saturated aq. NaHCO3. The aqueous layer was extracted with EtOAc (3×7 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to yield the desired compound (33 mg, 93%) as a white solid that was used without further purification.

Workup

  1. temperaturecooled to 0° C
  2. temperatureto warm to room temperature
  3. stirringstirred 22 h
  4. customThe reaction mixture was then quenched with water and saturated aq. NaHCO3
  5. extractionThe aqueous layer was extracted with EtOAc (3×7 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-edba2209b57f494aabb0a1e49e5249c2
Source dataset
uspto-grants-2016_08
Patent number
US09428500B2

Reaction notes

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