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

HRID 1374737Notes

Reaction equation

HRID 1374737 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-a9aaf758e5a04f67b3f18654fb3a1571
Source dataset
uspto-grants-2007_01
Patent number
US07166608B2

Reaction notes

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