Phenylacetyl chloride → HCID 23302083, compound

HRID 1952979Notes

Reaction equation

HRID 1952979 reaction equation
[C:1]1([CH2:7][N:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:22][CH2:23][CH2:24][NH2:25])[CH2:9][CH2:10][CH2:11][NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N([CH2:38][CH3:39])CC)C.[C:40]1([CH2:46][C:47](Cl)=[O:48])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)(Cl)Cl>[C:40]1([CH2:46][C:47]([NH:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:22][CH2:23][CH2:24][NH:25][C:47]([CH2:46][C:39]2[CH:38]=[CH:42][CH:41]=[CH:40][CH:45]=2)=[O:48])=[O:48])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 23302090N1,N8-Bis(3-aminopropyl)-N1,N8-bis(phenylmethyl)-1,8-octanediamine

Product 1

HCID 23302083HCID 23302083, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Cool a solution of 5,14-bis[(phenyl)methyl]-1,5,14,18-tetraazaoctadecane (2.2 g, 5 mmol) and triethylamine (2 g, 20 mmol) in chloroform (100 mL) in an ice bath. Add a solution of phenylacetyl chloride (2.3 g, 15 mmol) in chloroform (10 mL) dropwise. Allow the reaction to warm to room temperature and stir for 18 hours. Rinse the reaction with aqueous sodium bicarbonate, dry the organic layer over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (ethyl acetate, silica gel) to provide 1,18-bis[[(phenyl)methyl]carbonyl]-5,14-bis-[(phenyl)methyl]-1,5,14,18-tetraazaoctadecane (3 g) as a thick oil.

Workup

  1. customthe reaction
  2. washRinse
  3. customthe reaction with aqueous sodium bicarbonate
  4. dry with materialdry the organic layer over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under vacuum
  7. customPurify the residue by flash chromatography (ethyl acetate, silica gel)

Sources & evidence

ORD record
ord-3e052e3368e24a26a247189ab6958718
Source dataset
uspto-grants-2000_09
Patent number
US06114394

Reaction notes

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