Ethyl Acetate → 6-Benzyl-1,4-diazepan-6-ylamine

HRID 424290Notes

Reaction equation

HRID 424290 reaction equation
C([N:8]1[CH2:14][C:13]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([N+:15]([O-])=O)[CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].CCOC(C)=O>CO.[Pd]>[CH2:18]([C:13]1([NH2:15])[CH2:14][NH:8][CH2:9][CH2:10][NH:11][CH2:12]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 585998471,4-Dibenzyl-6-benzyl-6-nitro-1,4-diazepane

Product 1

HCID 593813086-Benzyl-1,4-diazepan-6-ylamineYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 500 ml flask, compound 5 (16.0 g, 38.5 mmol) was dissolved in methanol (100 mL); Pd/C (10%, 3.0 g, moistened with 0.5 ml water) was added at once followed by ammonium formate (24.0 g, 0.385 mol). The mixture was stirred and heated to reflux for 3 h. When the reaction is complete (TLC PET/AcOEt 9/1), the catalyst was removed by filtration on Celite®, and the filtrate evaporated in vacuo. The residue is redissolved in dichloromethane and washed with 5% aq. NaOH. The organic phase was then dried (Na2SO4) obtaining 6 (5.98 g, 76%) as light yellow oil. M.p.:. ESI-MS: 206 (MH+); (Calc. for C12H19N3: 205 u.m.a.).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. customthe catalyst was removed by filtration on Celite®
  4. customthe filtrate evaporated in vacuo
  5. dissolutionThe residue is redissolved in dichloromethane
  6. washwashed with 5% aq. NaOH
  7. dry with materialThe organic phase was then dried (Na2SO4)

Sources & evidence

ORD record
ord-1fad49aa354240adbca432487984a6dc
Source dataset
uspto-grants-2012_01
Patent number
US08105567B2

Reaction notes

Loading…