Triethylamine → HCID 62951367, compound

HRID 552760Notes

Reaction equation

HRID 552760 reaction equation
C([O:5][C:6](=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][NH2:16])(C)(C)C.[CH2:18](N(CC)CC)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][NH:7][C:6](=[O:5])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 204431481,4-Dioxane hydrochlorideHCID 23000607tert-Butyl {[2-(aminomethyl)phenyl]methyl}carbamate

Product 1

HCID 62951367HCID 62951367, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl[2-(aminomethyl)benzyl]carbamate (0.2 g, 0.93 mmol) and triethylamine (260 μL, 1.9 mmol) in DCM (10 mL) was added AC2O (0.285 g, 0.00279 mol) dropwise and the reaction stirred for 2 h at r.t. The reaction was concentrated, the residue dissolved in EtOAc (20 mL) then washed with saturated aq NaHCO3 (2×10 mL). The organic layer was dried (Na2SO4) and concentrated to give the crude product (0.25 g, 90%). To a solution of this in DCM (5 mL) was added 2 mL of 4M HCl/dioxane and the solution was stirred for 1 h. The reaction was concentrated to give the title compound (0.16 g, 95%) which was used without further purification.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue dissolved in EtOAc (20 mL)
  3. washthen washed with saturated aq NaHCO3 (2×10 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give the crude product (0.25 g, 90%)
  7. stirringthe solution was stirred for 1 h
  8. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-86db6f52bab34846b670dd2bcc4b7f07
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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