Piperidine → HCID 68546659, compound

HRID 1841881Notes

Reaction equation

HRID 1841881 reaction equation
[C:1]([CH2:3][C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:5])#[N:2].[CH3:15][N:16]([CH3:27])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH:20]=O.N1CCCCC1>N1C=CC=CC=1>[C:1]([C:3](=[CH:20][C:19]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:17]([N:16]([CH3:27])[CH3:15])[CH:18]=1)[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 12225606Benzaldehyde, 3-(dimethylamino)-4-methoxy-HCID 85875172HCID 85875172, compound

Product 1

HCID 68546659HCID 68546659, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.96 g (20 mMol 6-(2-cyan-acetylamino)hexanoic acid was dissolved in 27 ml pyridine. 3.64 g (20 mMol) 3-dimethylamino-4-methoxybenzaldehyde and 0.6 mL piperidine were added to the solution and the reaction mixture was stirred for 20 hours. After evaporation of the reaction mixture the residue was solved in 150 ml ethyl acetate and 150 ml water and the pH was adjusted with pure acetic acid to 4.2. The aqueous phase was extracted with ethyl acetate. The collected ethyl acetate phases were washed with NaCl-Solution, dried and evaporated. The residue was chromatographed on SiO2 with ethyl acetate under low pressure. The product was crystallized from little ethyl acetate.

Workup

  1. customAfter evaporation of the reaction mixture the residue
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe collected ethyl acetate phases were washed with NaCl-Solution
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on SiO2 with ethyl acetate under low pressure
  7. customThe product was crystallized from little ethyl acetate

Sources & evidence

ORD record
ord-11b227e362d247d6abe34ac0f6d8f0d4
Source dataset
uspto-grants-2015_02
Patent number
US08946129B2

Reaction notes

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