Acetic Acid → 359878-17-4

HRID 354137Notes

Reaction equation

HRID 354137 reaction equation
[CH3:1][OH:2].CN[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:12][N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.[BH3-][C:21]#[N:22].[Na+].[C:24]([OH:27])(=O)[CH3:25]>CO.C(O)(=O)C>[CH3:1][O:2][C:6]1[CH:11]=[CH:10][C:9]([CH2:25][C:24]([N:22]([CH2:21][C:9]2[CH:10]=[CH:11][C:6]([CH3:5])=[CH:7][CH:8]=2)[CH:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)=[O:27])=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 7669N-MethylbenzylamineHCID 740491-Methyl-4-piperidoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 9799308359878-17-4

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

Methanol (50 ml) was added to an Erlenmeyer flask and acetic acid was added under stirring until pH 5. Methylbenzylamine (1.0 g, 8.8 mmol) and 1-Methyl-4-piperidone (1.1 g, 8.8 mmol) were added to a 100 ml round-bottomed flask and dissolved in the methanol/acetic acid (40 ml) solution previously made. The reaction mixture was stirred for 5 min and NaCNBH3 (0.83 g, 13.2 mmol) was added slowly under stirring. After 20 hours the reaction was concentrated and transferred to a separatory funnel containing dichloromethane and distilled water. The aqueous phase was made basic by addition of Na2CO3. The aqueous phase was extracted twice with dichloromethane. The combined organic layers were collected and dried with Na2SO4. Concentration afforded the title compound. Yield (crude): 98%. UV/MS 89/88 (M+ 353), tr (A, MS) 3.982.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 5 min
  3. stirringunder stirring
  4. concentrationAfter 20 hours the reaction was concentrated
  5. customtransferred to a separatory funnel
  6. additioncontaining dichloromethane
  7. distillationdistilled water
  8. additionThe aqueous phase was made basic by addition of Na2CO3
  9. extractionThe aqueous phase was extracted twice with dichloromethane
  10. customThe combined organic layers were collected
  11. dry with materialdried with Na2SO4
  12. concentrationConcentration

Sources & evidence

ORD record
ord-d85096bf5ca24e459ba61de719fa2239
Source dataset
uspto-grants-2004_06
Patent number
US06756393B2

Reaction notes

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