1-(2,2-dimethylpropanoyl)piperazine → HCID 66907079, compound

HRID 1690634Notes

Reaction equation

HRID 1690634 reaction equation
[CH3:1][C:2]([CH3:12])([CH3:11])[C:3]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].[CH2:13]([O:15][C:16](=[O:38])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=2)=[C:21]([O:33]CCOC)[CH:20]=1)[CH3:14]>C1COCC1>[CH2:13]([O:15][C:16](=[O:38])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:8]3[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C:2]([CH3:12])([CH3:11])[CH3:1])[CH2:6][CH2:7]3)=[CH:27][CH:26]=2)=[C:21]([O:33][CH2:18][CH2:17][CH2:16][O:15][CH3:13])[CH:20]=1)[CH3:14]

Participants

4

Reactant 2

HCID 27614081-(2,2-dimethylpropanoyl)piperazineHCID 86761547HCID 86761547, compound

Product 1

HCID 66907079HCID 66907079, compoundYield 153.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,2-dimethyl-1-piperazin-1-yl-propan-1-one (37.45 mg, 0.22 mmol) in THF (2 mL) concentrated acetic acid (63 μL, 1.1 mmol), Ethyl-3-[4′-Formyl-2-(2-methoxy-ethoxy)-biphenyl-4-yl]-propionate (74 mg, 0.2 mmol) dissolved in THF (1 mL) and cyanoborhydride resin (123 mg, 0.3 mmol) was added. The reaction was shaken in a closed-vessel under argon at r.t. overnight. The mixture was filtered and dried under reduced pressure. The residue was redissolved in ethyl acetate (20 mL) and washed with an aqueous sodium hydrogen carbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered and dried under reduced pressure to give 80.6 mg of the titled compound.

Workup

  1. filtrationThe mixture was filtered
  2. customdried under reduced pressure
  3. dissolutionThe residue was redissolved in ethyl acetate (20 mL)
  4. washwashed with an aqueous sodium hydrogen carbonate solution (20 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-199d1d5dc1414ac6826f53e3168276c6
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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