Pentane → 2-n-Octyl-1-dodecylamine

HRID 628221Notes

Reaction equation

HRID 628221 reaction equation
I[CH2:2][CH:3]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C1(=O)[NH:26]C(=O)C2=CC=CC=C12.[K].CCCCC.O.NN>CN(C=O)C.C(O)C>[CH2:14]([CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2][NH2:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 8003PentaneHCID 24654Hydrazine hydrate (1:1)HCID 24194345Phthalimide potassium saltHCID 866914509-(Iodomethyl)nonadecane

Product 1

HCID 187619992-n-Octyl-1-dodecylamineYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

1-Iodo-2-octyldodecane (5.90 g, 14.5 mmol) and potassium phthalimide (2.94 g, 15.9 mmol) were dissolved in 25 mL of DMF and vigorously stirred for 72 h at 25° C. The reaction mixture was poured into 200 mL of pentane, and washed four times with 100 mL water. The mixture was then passed through a 3 cm silica gel plug, and concentrated to give a colorless oil. The oil was next dissolved in 150 mL of ethanol, and 4 mL of hydrazine hydrate were added, leading to a mixture which was heated to reflux overnight. The resulting precipitates were collected by filtration, dissolved in 100 mL water, and the solution was made alkaline by addition of 6 M NaOH (aq). The resulting mixture was dissolved in 200 mL pentane, washed four times with 100 mL of water, once with 70 mL of brine, dried over MgSO4, and concentrated to give a colorless oil (3.08 g, 72% yield). 1H NMR (CDCl3 500 MHz): δ: 2.60 (d, J=5.0 Hz, 2H), 2.00 (t, J=5.0 Hz, 1H), 1.30-1.20 (b, 32H), 0.89 (t, J=7.5 Hz, 6H); MS (EI): m/z (%) 297.34 (100) [M+]. Elemental Analysis (calc. C, 80.73; H, 14.57): found C, 80.78; H, 14.52.

Workup

  1. washwashed four times with 100 mL water
  2. concentrationconcentrated
  3. customto give a colorless oil
  4. temperaturewas heated
  5. temperatureto reflux overnight
  6. customThe resulting precipitates
  7. filtrationwere collected by filtration
  8. dissolutiondissolved in 100 mL water
  9. additionby addition of 6 M NaOH (aq)
  10. dissolutionThe resulting mixture was dissolved in 200 mL pentane
  11. washwashed four times with 100 mL of water
  12. dry with materialonce with 70 mL of brine, dried over MgSO4
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-eace45f66e41457c864cc76c8d1de092
Source dataset
uspto-grants-2016_04
Patent number
US09312492B2

Reaction notes

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