Acetic Acid → HCID 3153429, compound

HRID 929744Notes

Reaction equation

HRID 929744 reaction equation
[C:1]1([CH2:7][CH2:8]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.C(O)(=O)C.[BH3-]C#[N:24].[Na+]>CO.ClCCl>[CH3:8][CH:7]([NH:24][CH:14]1[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1001PhenethylamineHCID 740491-Methyl-4-piperidoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 3153429HCID 3153429, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent4×HCID 6344DichloromethaneSolvent

Procedure

DL-Phenylethylamine (606 mg, 5.0 mmol) was dissolved in 10 ml methanol and 1-Methyl-4-piperidone (566 mg, 5.0 mmol) in 10 ml methanol was added. Mixture was stirred and Acetic acid (˜0.75 ml) was added until pH˜5. NaCNBH3 (628 g, 10 mmol) was slowly added. Gas evolution observed. After magnetic stirring for 20 hrs methanol was partly removed on Rotavapor (40° C.). Ethylacetate, 2M NaOH and water were added until pH˜10. Phases were separated and aq. phase was then re-extracted with ethylacetate and dichloromethane. Combined organic phases were dried over MgSO4. Concentration on Rotavapor (40° C.) yielded 838 mg crude 47AKU-36. TLC (10% methanol in dichloromethane): Rf=0.3. HPLC-MS (Method A): M+=219.1 (UV/MS (%)=100/94).

Workup

  1. customwas partly removed on Rotavapor (40° C.)
  2. additionEthylacetate, 2M NaOH and water were added until pH˜10
  3. customPhases were separated
  4. extractionaq. phase was then re-extracted with ethylacetate and dichloromethane
  5. dry with materialCombined organic phases were dried over MgSO4
  6. concentrationConcentration on Rotavapor (40° C.)
  7. customyielded 838 mg crude 47AKU-36

Sources & evidence

ORD record
ord-e55faa78396e4c77aebb58b6491bf47f
Source dataset
uspto-grants-2016_03
Patent number
US09296694B2

Reaction notes

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