Benzylamine → HCID 11461445, compound

HRID 1006375Notes

Reaction equation

HRID 1006375 reaction equation
[CH:1]([CH:3]=[CH2:4])=O.[CH2:5]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>C1COCC1.C1CCN2C(=NCCC2)CC1>[CH2:5]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:4][CH2:3][CH2:1][NH:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 7847AcroleinHCID 14798Sodium HydroxideHCID 317384-Benzylpiperidine

Product 1

HCID 11461445HCID 11461445, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of acrolein (90%, 3.2 g, 57 mmol) in THF (2 ml) was dropwise added to a solution of 4-benzylpiperidine (10.0 g, 57 mmol) and DBU (85 μl, 0.57 mmol) in THF (10 ml) for 10 minutes at −20° C. under stirring. The mixture was stirred for an hour raising the temperature from −20° C. to −10° C. Benzylamine (6.1 g, 57 mmol) and triacetoxy sodium borohydride (24.2 g, 114 mmol) were added to the reaction mixture successively at −10° C., and the mixture was stirred for 19 hours raising the temperature to room temperature. An aqueous solution of 2N sodium hydroxide (100 ml) was added to the reaction mixture under ice cooling and the mixture was stirred for 30 minutes, and extracted with diethyl ether (100 ml, 80 ml×2). The organic phase was dried over magnesium sulfate (anhydrous), then concentrated under reduced pressure. The residue was dissolved in 2-propanol (50 ml) and to the solution was added a solution of 4N hydrogen chloride in ethyl acetate (50 ml) with stirring. The resulting precipitate was collected by filtration. The precipitate was washed with 2-propanol (20 ml×3) and dried under reduced pressure to give the title compound as a white crystal (6.5 g).

Workup

  1. stirringThe mixture was stirred for an hour
  2. temperatureraising the temperature from −20° C. to −10° C
  3. stirringthe mixture was stirred for 19 hours
  4. stirringthe mixture was stirred for 30 minutes
  5. extractionextracted with diethyl ether (100 ml, 80 ml×2)
  6. dry with materialThe organic phase was dried over magnesium sulfate (anhydrous)
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in 2-propanol (50 ml) and to the solution
  9. additionwas added a solution of 4N hydrogen chloride in ethyl acetate (50 ml)
  10. stirringwith stirring
  11. filtrationThe resulting precipitate was collected by filtration
  12. washThe precipitate was washed with 2-propanol (20 ml×3)
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-8f5f2799c952469fa30690db0ce23c31
Source dataset
uspto-grants-2004_09
Patent number
US06787650B1

Reaction notes

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