Benzyl succinimido carbonate → N-benzyloxycarbonyl-N-diethoxyethyl-6-(phenylbutoxy)hexylamine

HRID 1936215Notes

Reaction equation

HRID 1936215 reaction equation
[CH2:1]([O:3][CH:4]([O:24][CH2:25][CH3:26])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:2].[CH2:27]([O:34][C:35](ON1C(=O)CCC1=O)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC(C)=O>[CH2:27]([O:34][C:35]([N:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:24][CH2:25][CH3:26])=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 69996075N-diethoxyethyl-6-(4-phenylbutoxy)hexylamine

Product 1

HCID 69994289N-benzyloxycarbonyl-N-diethoxyethyl-6-(phenylbutoxy)hexylamineYield 100.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2,39 g (6,55 mmol) N-diethoxyethyl-6-(4-phenylbutoxy)hexylamine in 25 ml acetone is added 1.59 g (7.07 mmol) N-(benzyloxycarbonyloxy)succinimide. After allowing the mixture to stir for 2 hr at room temperature, acetone is removed by evaporation and 30 ml AcOEt are added thereto. The resulting mixture is washed three times with 30 ml H2O. Once separated, the AcoEt phase is dried on anhydrous Na2SO4 and evaporated to dryness, thereby yielding 3.28 g (99%) N-benzyloxycarbonyl-N-diethoxyethyl-6-(phenylbutoxy)hexylamine as an oil.

Workup

  1. customacetone is removed by evaporation and 30 ml AcOEt
  2. additionare added
  3. washThe resulting mixture is washed three times with 30 ml H2O
  4. customOnce separated
  5. dry with materialthe AcoEt phase is dried on anhydrous Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1bafafeb775d410ea20369b1fbfaba38
Source dataset
uspto-grants-2002_05
Patent number
US06388134B1

Reaction notes

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