Benzylamine → 1-(1,1-dimethylethyl)-N-(phenylmethyl)-4-Piperidinamine

HRID 20305

Reaction equation

HRID 20305 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:12]([NH:19][CH:8]1[CH2:9][CH2:10][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 738401-tert-Butyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 226479391-(1,1-dimethylethyl)-N-(phenylmethyl)-4-PiperidinamineYield 26.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-tert-butyl-4-oxopiperidine (3.6 g, 23.1), benzylamine (5.11 ml, 46.8 mmol), acetic acid (1.5 ml) and sodium triacetoxyborohydride (7.38 g, 34.8 mmol) was stirred at ambient for 2 days. Reaction mixture reduced in vacuo, residue partitioned between aqueous K2CO3 and EtOAc. The organic portion was dried (Na2SO4), filtered and reduced in vacuo. The residue was subjected to chromatography using CH2Cl2/MeOH/NH4OH (87/12/1) as the eluent to yield N-benzyl-1-tert-butylpiperidin-4-amine (1.5 g) (LC/MS: Rt 0.45, [M+H]+ 247).

Workup

  1. customReaction mixture
  2. custompartitioned between aqueous K2CO3 and EtOAc
  3. dry with materialThe organic portion was dried (Na2SO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-48e4777ee5c849119137dbc7f8327e03
Source dataset
uspto-grants-2010_06
Patent number
US07745638B2

Linked notes

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