Piperidine → HCID 68672115, compound

HRID 2047404Notes

Reaction equation

HRID 2047404 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:12]=[C:13]([N:17]2[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:12]=[C:13]([N:17]2[CH2:22][CH2:21][CH:20]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 68670890HCID 68670890, compound

Product 1

HCID 68672115HCID 68672115, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

1-[3-(1-methyl-1H-benzo[d]imidazol-2-yl)phenyl]piperidin-4-one (0.06 g, 0.2 mmol) and piperidine (0.034 g, 0.4 mmol) with triethylamine (27 μL, 0.2 mmol) and molecular sieves (0.5 g) were heated to 40° C. in methanol (5 ml) for 16 hours. Sodiumcyanoborohydride (0.025 g, 0.4 mmol) and zinc chloride (0.027 g, 0.2 mmol) were added and the reaction heated for a further 16 hours, the reaction mixture was evaporated and the residue partitioned between 1N sodium hydroxide (2 ml) and dichloromethane (4 ml). The organic layer was separated, evaporated and purified by preparative HPLC.

Workup

  1. temperaturethe reaction heated for a further 16 hours
  2. customthe reaction mixture was evaporated
  3. customthe residue partitioned between 1N sodium hydroxide (2 ml) and dichloromethane (4 ml)
  4. customThe organic layer was separated
  5. customevaporated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-3389a78a905749df893614f880a67df6
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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