Acetic Acid → HCID 89754535, compound

HRID 2173213Notes

Reaction equation

HRID 2173213 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH:12]=O)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C([BH3-])#N.[Na+].CC(O)=O>CO>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][N:17]2[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]2)=[CH:10][C:3]=1[O:2][CH3:1])#[N:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Product 1

HCID 89754535HCID 89754535, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(Methyloxy)-4-(2-oxoethyl)benzonitrile (200 mg, 1.142 mmol), tert-butyl piperazine-1-carboxylate (532 mg, 2.85 mmol), and SODIUM CYANOBOROHYDRIDE (717 mg, 11.4 mmol) were combined in a 50 mL Flask and dissolved in MeOH. The resulting mixture was then stirred for 10 minutes followed by addition of few drops of AcOH. The mixture was stirred for overnight. The reaction mixture was concentrated to dryness, re-dissolved in EtOAc and washed with saturated NaHCO3 solution, brine, and the organic layer was dried over Na2SO4, filtered and concentrated to dryness. The residue purified by MPLC to yield the title compound. LC-MS (IE, m/z): 346 [M+1]+;

Workup

  1. stirringThe mixture was stirred for overnight
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionre-dissolved in EtOAc
  4. washwashed with saturated NaHCO3 solution, brine
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue purified by MPLC

Sources & evidence

ORD record
ord-73f41e6038b04f93823d673f59685fe0
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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