1-Pyrrolidineethanamine → (Z,E,E)-N-(2-pyrrolidinoethyl)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraenamide

HRID 26981Notes

Reaction equation

HRID 26981 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.[NH2:24][CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>CN(C)C=O>[N:27]1([CH2:26][CH2:25][NH:24][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])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 86736493(Z,E,E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraenoic acid

Product 1

HCID 20342984(Z,E,E)-N-(2-pyrrolidinoethyl)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraenamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same manner as in Example 9, the reaction was conducted using 1.0 g of (E,Z,E), (E,E,E), (Z,Z,E) and (Z,E,E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraenoic acid and 450 mg of 1-(2-aminoethyl)pyrrolidine in 6.0 ml of N,N-dimethylformamide and the reaction mixture was extracted with chloroform. The chloroform layer was washed with aqueous sodium hydrogencarbonate and extracted with dilute hydrochloric acid. The hydrochloric acid layer was neutralized with sodium hydrogencarbonate and extracted with chloroform. The chloroform layer was washed with water, dried and the solvent was distilled off. The residue was purified by a column chromatography using alumina (20 g) to afford 1.0 g of the end product.

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. washThe chloroform layer was washed with aqueous sodium hydrogencarbonate
  3. extractionextracted with dilute hydrochloric acid
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by a column chromatography

Sources & evidence

ORD record
ord-217a141ecb3e4944bb726b6304f5f4f7
Source dataset
uspto-grants-1979_04
Patent number
US04151357

Reaction notes

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