Methanol → HCID 23512960, compound

HRID 2414910Notes

Reaction equation

HRID 2414910 reaction equation
[CH3:1][CH:2]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17]1([CH2:23][CH2:24]N)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN1CC[C:30](=[O:33])CC1.[BH3-]C#N.[Na+].C[OH:39]>ClCCl.C(O)(=O)C>[CH3:30][O:33][C:20]1[CH:21]=[CH:22][C:17]([CH2:23][C:24]([N:9]([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH3:1])[CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:39])=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 887Methanol4×HCID 1001PhenethylamineHCID 740491-Methyl-4-piperidoneHCID 3153429HCID 3153429, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 23512960HCID 23512960, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

4-Alpha-methylbenzylamino-1-methyl-piperidine (47AKU-36) 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-8f2b741c33f2406e95bcbec3d981ca9a
Source dataset
uspto-grants-2004_11
Patent number
US06815458B2

Reaction notes

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