Acetic Acid → Benzyl(cyclopropylmethyl)amine

HRID 1158420Notes

Reaction equation

HRID 1158420 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]1([CH2:12][NH2:13])[CH2:11][CH2:10]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([NH:13][CH2:12][CH:9]1[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 75646CyclopropanemethanamineHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 518069Benzyl(cyclopropylmethyl)amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of benzaldehyde (3 mL, 29.55 mmol), cyclopropanemethylamine (2.53 mL, 29.55 mmol), AcOH (1.7 mL, 29.55 mmol) in 1,2-dichloroethane (150 mL) is stirred at RT for 25 minutes. Sodium triacetoxyborohydride (8.8 g, 41.37 mmol) is added and the mixture further stirred overnight at RT. Sodium triacetoxyborohydride (3.13 g, 15 mmol) is again added to complete the reaction. The mixture is quenched by the addition of NaOH 1N (50 mL), the layers are separated and the aqueous phase is extracted twice with ether. The combined organic extracts are dried (Na2SO4), filtered and concentrated. The crude material is purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 95:5 to 80:20+5% NH3) to give the title product. tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.91 min.

Workup

  1. stirringthe mixture further stirred overnight at RT
  2. customthe reaction
  3. customThe mixture is quenched by the addition of NaOH 1N (50 mL)
  4. customthe layers are separated
  5. extractionthe aqueous phase is extracted twice with ether
  6. dry with materialThe combined organic extracts are dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material is purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 95:5 to 80:20+5% NH3)

Sources & evidence

ORD record
ord-4d7e4be483ff45e49e9062584846b416
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

Loading…