Hydrochloric Acid → 4-(2-Morpholin-4-yl-ethoxy)-benzamidine

HRID 1175146Notes

Reaction equation

HRID 1175146 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Li][N:19]([Si](C)(C)C)[Si](C)(C)C.Cl>C1COCC1>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]([NH2:19])=[NH:15])=[CH:12][CH:11]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 29940744-(2-Morpholin-4-ylethoxy)benzonitrileHCID 178418261HCID 178418261, compound

Product 1

HCID 283949444-(2-Morpholin-4-yl-ethoxy)-benzamidineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(2-Morpholin-4-yl-ethoxy)-benzonitrile (Maybridge CC 42116)(2.7 g; 11.64 mmol) in THF (10 ml) is combined with LiN(TMS)2 (30 mmol; 30 ml of a 1M solution in THF) and stirred for 30 minutes at 55° C., kept at room temperature for 30 minutes and cooled to 5° C., while 3N HCl (28 ml) is added slowly. After 10 minutes the reaction mixture is washed with TBME and the aqueous phase is adjusted to pH ˜11 with solid NaOH, saturated with solid K2CO3 and extracted with TBME/MeOH (˜10:1) several times. The combined organic phases are dried over Na2SO4, filtered and evaporated to yield the title compound as yellow crystals (2.7 g; 93%). 1H-NMR (400 MHz; DMSO-d6): 7.72 (d, 2H); 6.96 (d, 2H); 6.31 (bs, 3H); 4.13 (t, 2H); 3.59 (m, 4H); 2.71 t, 2H); 2.49 (m, 4H). MS (m/z) ES+: 250 (MH+).

Workup

  1. additionis added slowly
  2. washAfter 10 minutes the reaction mixture is washed with TBME
  3. extractionextracted with TBME/MeOH (˜10:1) several times
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3601e3956bd24c9eb731d21860811e33
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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