1-Bromooctane → N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamine

HRID 525980

Reaction equation

HRID 525980 reaction equation
[C:1]1([NH2:12])[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.[I-].[K+]>[CH2:14]([N:12]([CH2:9][CH2:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 167201,5-Diaminonaphthalene

Product 1

HCID 68441382N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamineYield 38.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

Naphthalene-1,5-diamine (3.14 g, 19.8 mmol), 1-bromooctane (25.25 g, 0.130 mol), potassium carbonate (11.79 g, 85.3 mmol), and potassium iodide (0.05 g, 0.30 mmol) was stirred in dry butanol (150 ml) and heated to 110° C. for 36 h. The reaction was quenched with water and extracted with ether three times. The combined organic phase was washed three times with water and evaporated to give black oil which was distilled under reduced pressure at 90° C. to yield a black tar. This was purified with flash chromatography using hexane as mobile phase to obtain colourless oil which crystallised to yield N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamine (2.3 g, 3.79 mmol) as white crystals. 1H-NMR (CDCl3, δ): 0.85 (t, 12H), 1.0-1.4 (m, 40H), 1.4-1.6 (m, 8H), 3.08 (t, 8H), 7.1 (d, 2H), 7.35 (t, 2H), 8.01 (d, 2H) MS MALDI-TOF (m/z): 606.574

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ether three times
  3. washThe combined organic phase was washed three times with water
  4. customevaporated
  5. customto give black oil which
  6. distillationwas distilled under reduced pressure at 90° C.
  7. customto yield a black tar
  8. customThis was purified with flash chromatography
  9. customto obtain colourless oil which
  10. customcrystallised

Sources & evidence

ORD record
ord-e20de384567c4138967ddc336962212b
Source dataset
uspto-grants-2016_05
Patent number
US09343198B2

Linked notes

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