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

HRID 1897379

Reaction equation

HRID 1897379 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-cc4cbe8c62b2426983183ff61b6f89b8
Source dataset
uspto-grants-2013_08
Patent number
US08519037B2

Linked notes

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