Hexane → [3,6-Dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-ethyl-propyl-amine

HRID 1737680Notes

Reaction equation

HRID 1737680 reaction equation
[CH3:1][C:2]1[C:3]([O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])=[N:4][C:5]([CH3:11])=[CH:6][C:7]=1[NH:8][CH2:9][CH3:10].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:32][CH2:33]CCCC.I[CH2:39]CC>C1COCC1>[CH3:1][C:2]1[C:3]([O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])=[N:4][C:5]([CH3:11])=[CH:6][C:7]=1[N:8]([CH2:32][CH3:33])[CH2:9][CH2:10][CH3:39]

Participants

6

Reactant 4

HCID 8058HexaneHCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 21912407[3,6-Dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-ethylamine

Product 1

HCID 9949271[3,6-Dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-ethyl-propyl-amineYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3,6-dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4yl]-ethyl-amine (7.00 g, 24.6 mmol) in 100 ml of dry THF was added 1.0 M lithium bis(trimethylsilyl)amide in hexane (32 ml, 32 mmol) at -78° C. After stirring at that temperature for 10 min, the reaction mixture was treated with iodopropane (13 ml, 125 mmol) at -70° C. After stirring at that temperature for 20 min, the dry ice bath was removed and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give an oil. The oil residue was purified through silica gel column chromatography using 1:1 chloroform:hexane to chloroform as eluent to give 5.04 g (62.5%) of [3,6-dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-ethyl-propyl-amine as yellow solid; 1H NMR (CDCl3) δ6.88 (s, 2H), 6.41 (s, 1H), 3.11(q,2H), 3.03(dd,2H), 2.30 (s, 3H), 2.25 (s, 3H), 2.19 (s, 3H), 2.07 (s, 6H), 1.55 (m, 2H), 1.08 (t, 3H), 0.90 (t, 3H) ppm. The corresponding HCl salt, white crystals; mp 167-169° C.; 1H NMR (MeOH-d4) δ7.00 (s, 2H), 6.75 (s, 1H), 3.54(q,2H), 3.43 (t, 2H), 2.35 (s, 3H), 2.31 (s, 3H), 2.27 (s, 3H), 2.08 (s, 6H), 1.69 (m, 2H), 1.25 (t, 3H0, 0.94 (t, 3H) ppm;

Workup

  1. stirringAfter stirring at that temperature for 20 min
  2. customthe dry ice bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 3 hours
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customto give an oil
  9. customThe oil residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-8fafa6c0a55c4e97acf7cec40a1082b1
Source dataset
uspto-grants-1999_10
Patent number
US05962479

Reaction notes

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