Palmitoyl chloride → HCID 86752669, compound

HRID 1418829Notes

Reaction equation

HRID 1418829 reaction equation
[OH:1][CH:2]([CH2:16][NH:17][CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:3][O:4][CH2:5][CH:6]([OH:15])[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13].C(N([CH2:29][CH3:30])CC)C.[C:31](Cl)(=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>C(Cl)Cl>[O:47]=[C:31]([N:8]([CH2:9][CH2:10][CH2:11][N:12]([CH3:13])[CH3:14])[CH2:7][CH:6]([OH:15])[CH2:5][O:4][CH2:3][CH:2]([OH:1])[CH2:16][N:17]([C:31](=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:29][CH3:30])[CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 15376645HCID 15376645, compound

Product 1

HCID 86752669HCID 86752669, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis(2-hydroxy-8-methyl-4,8-diazanonyl)ether (10 g, 0.030 mol) synthesized using a known method, triethylamine (6.1 g, 0.060 mol), and methylene chloride (200 ml) were placed in a 500 ml four-necked round flask, and the mixture was cooled on ice. Hexadecanoylchloride (16.5 g, 0.060 mol) was added dropwise over 1 hour to the flask while the contents of the flask were stirred under nitrogen. The mixture was stirred for 24 more hours at room temperature. The solid which precipitated was removed by filtration, after which water was added for washing. Methylene chloride was removed from the organic phase under reduced pressure. The residue was purified by column chromatography (packed with Kieselgel 60 (product of Merck), eluent: chloroform/methanol=7:1 (v/v)) to obtain 4.9 g of bis(4-(1-oxohexadecyl)-2-hydroxy-8-methyl-4,8-diazanonyl)ether. Yield: 20 wt %.

Workup

  1. customwere placed in a 500 ml four-necked round flask
  2. temperaturethe mixture was cooled on ice
  3. stirringThe mixture was stirred for 24 more hours at room temperature
  4. customThe solid which precipitated
  5. customwas removed by filtration
  6. additionafter which water was added
  7. washfor washing
  8. customMethylene chloride was removed from the organic phase under reduced pressure
  9. customThe residue was purified by column chromatography (packed with Kieselgel 60 (product of Merck), eluent: chloroform/methanol=7:1 (v/v))

Sources & evidence

ORD record
ord-7a3c400902904a23b799f54d1c8686ef
Source dataset
uspto-grants-1999_03
Patent number
US05885955

Reaction notes

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