Triethylamine → HCID 18764648, compound

HRID 480544Notes

Reaction equation

HRID 480544 reaction equation
C([O:4][CH2:5][C:6](Cl)=[O:7])(=O)C.[CH2:9]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][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][CH3:45])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].CCN(CC)CC.[OH-].[Na+]>C(Cl)(Cl)Cl.O.CO>[OH:4][CH2:5][C:6]([N:27]([CH2:28][CH2:29][CH2:30][CH2:31][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][CH3:45])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:7]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 26297Acetoxyacetyl chlorideHCID 66989Dioctadecylamine

Product 1

HCID 18764648HCID 18764648, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

(Acetyloxy)acetyl chloride (3.8 g; 28.1 mmol) (commercial product) dissolved in CHCl3 (150 mL) was added dropwise to a solution of dioctadecylamine (13.3 g; 25.5 mmol) and Et3N (3.9 mL; 28.1 mmol) in CHCl3 (350 mL) and the solution was stirred at room temperature overnight. MeOH (250 mL) and 2 N NaOH (50 mL) were added to the solution. H2O was added to the reaction mixture and a two phase system was obtained. The lower organic layer was separated and evaporated. The solid residue was suspended in n-hexane and filtered to give the desired compound (12.1 g;20.9 mmol). Yield 82%. HPLC: 96% (area %). K.F.: <0.1%. The 13C-NMR, MS and IR spectra were consistent with the structure.

Workup

  1. customa two phase system was obtained
  2. customThe lower organic layer was separated
  3. customevaporated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-adacfd2df7e640008f5c3f6e857d69ab
Source dataset
uspto-grants-2003_11
Patent number
US06652834B2

Reaction notes

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