Phenylacetyl chloride → HCID 23302083, compound

HRID 862791Notes

Reaction equation

HRID 862791 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

Chill a solution of 5,14-bis[(phenyl)methyl]-1,5,14,18-tetraazaoctadecane (2.2 g, 5 mmole) and triethylamine (2 g, 20 mmole) in chloroform (100 ml) in an ice bath. Add a solution of phenylacetyl chloride (2.3 g, 15 mmole) in chloroform (10 ml) dropwise. Remove the ice bath and stir the mixture at ambient temperature for 18 hours. Extract the reaction mixture with aqueous sodium bicarbonate, dry the organic layer and evaporate. Chromatograph the residue on a flash silica gel column (ethyl acetate) to give 3 g of the desired product as a thick oil.

Workup

  1. customRemove the ice bath
  2. extractionExtract the reaction mixture with aqueous sodium bicarbonate
  3. customdry the organic layer
  4. customevaporate

Sources & evidence

ORD record
ord-b906c76082a54f02afb60b9aebd2371d
Source dataset
uspto-grants-1998_02
Patent number
US05719193

Reaction notes

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