Sodium Azide → 1-Benzyl-3-methyl-1,4-diazepan-5-one

HRID 1867386Notes

Reaction equation

HRID 1867386 reaction equation
[N-:1]=[N+]=[N-].[Na+].[CH2:5]([N:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH:14]([CH3:19])[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(OCC)(=O)C>[CH2:5]([N:12]1[CH2:17][CH2:16][C:15](=[O:18])[NH:1][CH:14]([CH3:19])[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 5609651-Benzyl-3-methyl-4-piperidone

Product 1

HCID 684323731-Benzyl-3-methyl-1,4-diazepan-5-oneYield 49%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium azide (1.58 g, 24.4 mmol) was added portionwise over 6 h to a solution of 1-benzyl-3-methylpiperidin-4-one (5.00 g, 24.4 mmol) at 0° C., then the reaction mixture was allowed to reach room temperature over 16 h. The reaction mixture was then poured upon ice/40% aq. sodium hydroxide solution/ethyl acetate, the organic layer was washed with brine, dried (MgSO4), and evaporated. Recrystallization in n-heptane/ethyl acetate 2:1 (60 ml) produced the title compound (2.59 g, 49%). White solid, MS: 219.3 (MH+).

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customRecrystallization in n-heptane/ethyl acetate 2:1 (60 ml)

Sources & evidence

ORD record
ord-981921c094f645808d5630774fb747c9
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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