Acetic Acid → Benzyl-(3-methyl-2-phenyl-butyl)-amine

HRID 1698304Notes

Reaction equation

HRID 1698304 reaction equation
[CH3:1][CH:2]([CH3:12])[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][NH2:5].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:13]([NH:5][CH2:4][CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]([CH3:12])[CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240Benzaldehyde2×HCID 5049666Sodium triacetoxyborohydrideHCID 98802173-Methyl-2-phenylbutan-1-amine2×

Product 1

HCID 67273216Benzyl-(3-methyl-2-phenyl-butyl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound is prepared from 3-methyl-2-phenyl-butylamine and benzaldehyde: A solution of 3-methyl-2-phenyl-butylamine (1.3 g, 8 mmol) and benzaldehyde (0.81 mL, 8 mmol) in CH2Cl2 (50 mL) is stirred at RT for 20 min. Sodium triacetoxyborohydride (2.52 g, 11.3 mmol) is then added, followed by acetic acid (0.46 mL, 8 mmol). The reaction mixture is stirred at RT for 16 h, then quenched by the addition of saturated NaHCO3 solution. The organic layer is separated and the aqueous phase is extracted twice with CH2Cl2. The combined organic layers are dried (Na2SO4) and evaporated. The residue is purified by flash chromatography (hexane/ethyl acetate) to afford benzyl-(3-methyl-2-phenyl-butyl)-amine as a colourless oil. MS: 254.3 [M+H]+; tR (HPLC, C18 column; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.03 min.

Workup

  1. customquenched by the addition of saturated NaHCO3 solution
  2. customThe organic layer is separated
  3. extractionthe aqueous phase is extracted twice with CH2Cl2
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. customevaporated
  6. customThe residue is purified by flash chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2c418fc8da4b4f99809296bcc99867fc
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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