Acetic Acid → tert-Butyl 4-(benzylamino)piperidine-1-carboxylate

HRID 899783Notes

Reaction equation

HRID 899783 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 15380687tert-Butyl 4-(benzylamino)piperidine-1-carboxylateYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Boc-piperidone (3.0 g, 15.1 mmol) in THF (76 mL) was added benzylamine (1.65 mL, 15.1 mmol), acetic acid (0.86 mL, 15.1 mmol) and sodium triacetoxyborohydride (4.8 g, 22.6 mmol). After stirring 2.5 hours the reaction mixture was concentrated under reduced pressure and CH2Cl2 (50 mL) and saturated aqueous NaHCO3 solution (50 mL) was added. The organic phase was separated, and the aqueous was extracted with CH2Cl2 (2×50 mL). The combined organic phases were then dried (MgSO4), filtered, and concentrated under reduced pressure to afford 4-benzylamino-piperidine-1-carboxylic acid tert-butyl ester (4.30 g, 98%).

Workup

  1. concentrationwas concentrated under reduced pressure and CH2Cl2 (50 mL) and saturated aqueous NaHCO3 solution (50 mL)
  2. additionwas added
  3. customThe organic phase was separated
  4. extractionthe aqueous was extracted with CH2Cl2 (2×50 mL)
  5. dry with materialThe combined organic phases were then dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a6da8f9803d4803964d25802e2c8b08
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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