Dimethylformamide → Benzyl 1,4-diazepane-1-carboxylate

HRID 1587192Notes

Reaction equation

HRID 1587192 reaction equation
CN(C)C=O.[NH:6]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(=O)(O)[O-].[Na+].[CH2:18]([O:25][C:26](Cl)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[CH2:18]([O:25][C:26]([N:6]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10387Benzyl chloroformateHCID 68163Hexahydro-1,4-diazepineHCID 516892Sodium Bicarbonate

Product 1

HCID 4384955Benzyl 1,4-diazepane-1-carboxylateYield 65.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 230 ml of dimethylformamide were added 25 g of homopiperazine and 5.4 g of sodium bicarbonate and then 25 ml of water followed by dropwise addition of 10 g of benzyloxycarbonyl chloride with stirring under ice cooling, and the mixture was stirred at a room temperature overnight. After evaporating off dimethylformamide under a reduced pressure, the reaction mixture was extracted three times with 100 ml of chloroform, and the extract was dried over magnesium sulfate and evaporated to remove the solvent under a reduced pressure. The resulting residue was applied to a silica gel column and eluted with chloroform/methanol (9:1), to obtain 9 g of the title compound as a light yellow liquor liquid.

Workup

  1. stirringthe mixture was stirred at a room temperature overnight
  2. customAfter evaporating off dimethylformamide under a reduced pressure
  3. extractionthe reaction mixture was extracted three times with 100 ml of chloroform
  4. dry with materialthe extract was dried over magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under a reduced pressure
  7. washeluted with chloroform/methanol (9:1)

Sources & evidence

ORD record
ord-12f2f68481c64417a521425846f1e93f
Source dataset
uspto-grants-1993_06
Patent number
US05216150

Reaction notes

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