Benzylamine → (E,E,E)-N-benzyl-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraenamide

HRID 26979Notes

Reaction equation

HRID 26979 reaction equation
[OH:1][CH2:2]/[C:3](/[CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:4]/[CH2:5][CH2:6]/[C:7](/[CH3:12])=[CH:8]/[C:9]([OH:11])=O.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C(OCC)(=O)C.C(OCC)C>[CH2:24]([NH:31][C:9](=[O:11])/[CH:8]=[C:7](\[CH3:12])/[CH2:6][CH2:5]/[CH:4]=[C:3](/[CH2:2][OH:1])\[CH2:13][CH2:14]/[CH:15]=[C:16](\[CH3:23])/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 86736491(E,E,E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraenoic acid

Product 1

HCID 70585507(E,E,E)-N-benzyl-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraenamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.0 g of (E,Z,E) and (E,E,E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraenoic acid in 10 ml of ethyl acetate were added 0.41 ml of benzylamine, 0.84 ml of diphenylphosphoric acid azide and then 0.5 ml of triethylamine under ice-cooling and the reaction mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was diluted with ethyl ether, washed successively with dilute hydrochloric acid, aqueous sodium hydrogencarbonate and water and dried over anhydrous sodium sulfate. The solvent was distilled off to give an oily substance, which was then purified by a column chromatography using silica gel (25 g) to afford 960 mg of the end product.

Workup

  1. customAfter completion of the reaction
  2. washwashed successively with dilute hydrochloric acid, aqueous sodium hydrogencarbonate and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customto give an oily substance, which
  6. customwas then purified by a column chromatography

Sources & evidence

ORD record
ord-2b16cd3cdce943779397052d39891604
Source dataset
uspto-grants-1979_04
Patent number
US04151357

Reaction notes

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