Hydrazine hydrate (1:1) → 2-n-Octyl-1-dodecylamine

HRID 536990Notes

Reaction equation

HRID 536990 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].O.NN>CN(C=O)C.CCCCC.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 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8003PentaneSolvent

Conditions

Temperature
25 °C

Procedure

Iodoalkane 5 (5.90 g, 14.5 mmol) and potassium phthalimide (2.94 g, 15.9 mmol) were taken up in 25 mL of DMF and vigorously stirred for 72 hours at 25° C. The reaction mixture was then taken up in 200 mL of pentane, washed four times with 100 mL of water, passed through a 3 cm silica gel plug, and concentrated to give a colorless oil. The oil was next taken up in 150 mL of ethanol, 4 mL of hydrazine hydrate was added, and the mixture was heated at reflux overnight. The resulting precipitate was collected by filtration, dissolved in 100 mL of water, and the solution was made alkaline by the addition of 6 M NaOH (aq). The resulting mixture was then taken up in 200 mL of pentane, washed four times with 100 mL of water, once with 70 mL of brine, and concentrated to give a colorless oil (3.08 g, 72% yield). Anal. Calcd. for C20H43N: C, 80.73; H, 14.57. Found: C, 80.78; H, 14.52; 1H NMR (CDCl3): 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+].

Workup

  1. washwashed four times with 100 mL of water
  2. concentrationconcentrated
  3. customto give a colorless oil
  4. temperaturethe mixture was heated
  5. temperatureat reflux overnight
  6. filtrationThe resulting precipitate was collected by filtration
  7. dissolutiondissolved in 100 mL of water
  8. additionby the addition of 6 M NaOH (aq)
  9. washwashed four times with 100 mL of water
  10. concentrationonce with 70 mL of brine, and concentrated

Sources & evidence

ORD record
ord-45aaa438ea924d2d9134811a1ca4d7a0
Source dataset
uspto-grants-2014_10
Patent number
US08859714B1

Reaction notes

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