Benzaldehyde → HCID 58852302, compound

HRID 1716567Notes

Reaction equation

HRID 1716567 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[NH2:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.S([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=3[N:22]=[C:23]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 23665763Sodium BisulfiteHCID 588522881,1-Dimethylethyl 4-[(2-amino-4-methylphenyl)amino]-1-piperidinecarboxylate

Product 1

HCID 58852302HCID 58852302, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a small pressure bottle was placed 4-(2-amino-4-methyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester, benzaldehyde (92 μL, 0.90 mmol), sodium hydrogensulfite (147 mg, 1.48 mmol) in DMF (5 mL). The bottle was sealed and heated at 100° C. for two hours and then stirred at 25° C. overnight for 16 hours. The reaction mixture was then concentrated in vacuo and partitioned between ethyl acetate (15 mL) and brine/water (1:1, 15 mL). The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. Flash chromatography (Biotage 40S column, 40/60 ethyl acetate/hexanes) afforded 4-(5-methyl-2-phenyl-benzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (339 mg, quantitative) as a light purple foam.

Workup

  1. customThe bottle was sealed
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. custompartitioned between ethyl acetate (15 mL) and brine/water (1:1, 15 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79c544b19a884d08ac8afd55062de7aa
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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