Benzaldehyde → Benzyl-(3-methyl-2-phenyl-butyl)-amine

HRID 1698306Notes

Reaction equation

HRID 1698306 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.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[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

7

Reactant 4

HCID 240Benzaldehyde2×HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 98802173-Methyl-2-phenylbutan-1-amine

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-methyl-2-phenyl-butylamine (1.3 g, 8 mmol), benzaldehyde (271 μL, 2.66 mmol) and CH2Cl2 (50 mL) is stirred for 20 min at RT. NaBH(OAc)3 (840 mg, 3.96 mmol) and acetic acid (154 μL, 2.69 mmol) are added. After 2 h the same amounts as indicated above of benzaldehyde, NaBH(OAc)3 and acetic acid are added once again. This procedure is repeated after 4 h. After stirring for 16 h at RT, saturated NaHCO3 solution is added, the CH2Cl2 layer is removed and the aqueous phase is extracted twice with fresh CH2Cl2. The combined organic layers are dried (Na2SO4), evaporated in vacuo and the residue is purified by flash chromatography (hexane/ethyl acetate). The combined pure fractions are evaporated to afford the title compound as a colourless oil. MS: 254.3 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.03 min.

Workup

  1. additionare added once again
  2. waitThis procedure is repeated after 4 h
  3. stirringAfter stirring for 16 h at RT
  4. customthe CH2Cl2 layer is removed
  5. extractionthe aqueous phase is extracted twice with fresh CH2Cl2
  6. dry with materialThe combined organic layers are dried (Na2SO4)
  7. customevaporated in vacuo
  8. customthe residue is purified by flash chromatography (hexane/ethyl acetate)
  9. customThe combined pure fractions are evaporated

Sources & evidence

ORD record
ord-02b6cf03594a427abda63cc9c81bd0bf
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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