Triethylamine → HCID 11454242, compound

HRID 1936214Notes

Reaction equation

HRID 1936214 reaction equation
Br.[CH3:2][O:3][CH:4]([O:24][CH3:25])[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.C(N(CC)CC)C.[CH2:33]([O:40][C:41](ON1C(=O)CCC1=O)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CC(C)=O>[CH2:33]([O:40][C:41]([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:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][CH:4]([O:3][CH3:2])[O:24][CH3:25])=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 69993910HCID 69993910, compound

Product 1

HCID 11454242HCID 11454242, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4.15 g (9.93 mmol) N-dimethoxyethyl-6-(4-phenylbutoxy)hexylamine hydrobromide in 40 ml acetone is added 1.4 ml triethylamine and 2.41 g (10.71 mmol) N-(benzyloxycarbonyloxy)succinimide. After allowing the mixture to stir for 2 hr at room temperature, acetone is evaporated of f and 40 ml Et2O is added thereto. The resulting mixture is washed three times with 40 ml H2O. Once separated, the ether phase is dried on anhydrous Na2SO4 and evaporated to dryness, to yield 4.46 g (95.3%) N-benzyloxycarbonyl-N-dimethoxyethyl-6-(4-phenylbutoxy)hexylamine as an oil.

Workup

  1. customacetone is evaporated of f and 40 ml Et2O
  2. additionis added
  3. washThe resulting mixture is washed three times with 40 ml H2O
  4. customOnce separated
  5. dry with materialthe ether phase is dried on anhydrous Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1e7afa6f492545c8a015c29d4d96f24a
Source dataset
uspto-grants-2002_05
Patent number
US06388134B1

Reaction notes

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