Benzaldehyde → N-Benzyl-N'-boc-ethylenediamine

HRID 750464Notes

Reaction equation

HRID 750464 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14](=[O:19])[NH:15][CH2:16][CH2:17][NH2:18])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClCCl>ClCCCl>[C:9]([O:13][C:14](=[O:19])[NH:15][CH2:16][CH2:17][NH:18][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6344DichloromethaneHCID 187201N-BOC-ethylenediamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10634443N-Benzyl-N'-boc-ethylenediamineYield 60.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Benzaldehyde (3.3 ml, 32.4 mmol) was added to a stirred solution of tert-butyl-N-(2-aminoethyl)carbamate (5.19 g, 32.4 mmol) in 1,2-dichloroethane (50 ml). After stirring for 1 h sodium triacetoxyborohydride (10.3 g, 48.6 mmol) was added in two portions and the reaction mixture stirred at room temperature for a further 3 h. Dichloromethane (300 ml) was added and the mixture washed with 1N sodium hydroxide. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 50-100% ethyl acetate in hexane then 1-5% methanol in ethyl acetate to afford the title compound (4.9 g, 60%). Mass spectrum (AP+): Found 251 (MH+). C14H22N2O2 requires 250.

Workup

  1. additionwas added in two portions
  2. washthe mixture washed with 1N sodium hydroxide
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 50-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4ea072d4bd4341289136a2c8aa1b5ec0
Source dataset
uspto-grants-2008_07
Patent number
US07405217B2

Reaction notes

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