Sodium Hydroxide → HCID 68959425, compound

HRID 354156Notes

Reaction equation

HRID 354156 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH:15]2[CH2:16][C:17]([CH2:19][CH:12]1[CH2:13][CH2:14]2)=O.[BH3-]C#N.[Na+].[OH-].[Na+]>CO.ClCCl.O.C(O)(=O)C>[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][CH:16]2[C@H:15]3[N:11]([CH3:10])[C@H:12]([CH2:13][CH2:14]3)[CH2:19][CH2:17]2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 660354-MethylbenzylamineHCID 79038Npc164516HCID 5003444Sodium cyanoborohydride

Product 1

HCID 68959425HCID 68959425, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolvent3×HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-Methylbenzylamine (607 mg, 5.0 mmol) was dissolved in 10 ml methanol and placed in 100 ml flask. Tropinone (697 mg, 5.0 mmol) in 10 ml methanol was added. Acetic acid (0.75 ml) was added until pH˜5. NaCNBH3 (628 mg, 10 mmol) was slowly added. Gas evolution observed. After 20 hrs magnetic stirring dichloromethane, 2M NaOH and water were added until pH˜10. Phases were separated and aq. phase was then re-extracted with dichloromethane. Combined organic phases were dried over MgSO4. Concentration on Rotavapor (40° C.) yielded 1.14 g crude 47AKU-17. TLC (10% methanol in dichloromethane): Rf =0.4. HPLC-MS (Method A): M+=245.2 (UV/MS(%)=65/96).

Workup

  1. customplaced in 100 ml flask
  2. additionwere added until pH˜10
  3. customPhases were separated
  4. extractionaq. phase was then re-extracted with dichloromethane
  5. dry with materialCombined organic phases were dried over MgSO4
  6. concentrationConcentration on Rotavapor (40° C.)
  7. customyielded 1.14 g crude 47AKU-17

Sources & evidence

ORD record
ord-95514a099f4548a6be414f418dc88d10
Source dataset
uspto-grants-2004_06
Patent number
US06756393B2

Reaction notes

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