Propylamine → 2-(n-Decyl)imidazoline

HRID 1488794Notes

Reaction equation

HRID 1488794 reaction equation
[C:1](#[N:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Li].[CH2:14]([NH2:17])[CH2:15]C>C(N)CN>[CH2:2]([C:1]1[NH:12][CH2:15][CH2:14][N:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 7852Propylamine2×HCID 16722Undecanenitrile2×HCID 3028194Lithium

Product 1

HCID 114994602-(n-Decyl)imidazolineYield 22%

Reagents, catalysts & solvents 1

HCID 3301EthylenediamineSolvent2×

Procedure

Reduction of undecanenitrile in n-propylamine and ethylene-diamine. Lithium, (0.21 g, 30 mmol) in small pieces, was added to a stirred solution of undecanenitrile (0.84 g, 5 mmol) in n-propylamine and ethylenediamine (1.0 mL). The temperature began to rise after 20 min and reached 32° after 30 min and the reaction mixture turned blue. An aliquot of the reaction mixture showed no nitrile by glpc. The reaction mixture was poured over crushed ice and extracted with ethyl acetate (2×50 mL). After distillation of the ethyl acetate the residue deposited crystals. The crystals were collected and dried to give 2-(n-decyl)imidazoline (0.23 g, 22%)

Workup

  1. waitreached 32° after 30 min
  2. additionThe reaction mixture was poured
  3. customover crushed ice
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. distillationAfter distillation of the ethyl acetate the residue
  6. customThe crystals were collected
  7. customdried

Sources & evidence

ORD record
ord-e673198c27d0401f99ebe5ce08e77232
Source dataset
uspto-grants-1997_10
Patent number
US05675038

Reaction notes

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