Ammonium Chloride → 4-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine

HRID 1014190Notes

Reaction equation

HRID 1014190 reaction equation
[I-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH:18]=[CH:17][N+:16]([CH2:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH:14]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 666496524-(3-Methoxy-4-nitrophenyl)-1-propylpyridinium iodide

Product 1

HCID 598602684-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridineYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-10 °C

Procedure

4-(3-methoxy-4-nitrophenyl)-1-propylpyridinium iodide (10 g, 25 mmol) was dissolved in methanol (200 mL). As the mixture was cooled to −10° C. the starting material started to precipitated out of the solution. Sodium borohydride (4.61 g, 11.3 mmol) was added in ˜500 mg portions. Effervescence was observed during the addition as dissolution of the solids in the reaction was observed. The reaction was stirred for 2 h at −10° C. when analysis by TLC revealed completion of the reaction. Saturated aqueous ammonium chloride was added and the reaction warmed to room temperature. The mixture was extracted with Ethyl acetate, the organic layers were dried (Mg2SO4), filtered, and concentrated in vacuo to provide 4-(3-methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine (6.7 g, 97% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.88 (t, J=7.4 Hz, 3 H), 1.50 (dt, J=7.3, 7.3 Hz, 2 H), 2.37 (t, J=7.2 Hz, 2 H), 2.53 (m, 2 H), 2.63 (m, 2 H), 3.11 (br s, 2H), 3.96 (s, 3 H), 6.43 (t, J=3.5 Hz, 1 H), 7.16 (dd, J=8.4, 1.5 Hz, 1 H), 7.29 (d, J=1.3 Hz, 1 H), 7.86 (d, J=8.6 Hz, 1 H). ESIMS (M+H)+=277.

Workup

  1. customto precipitated out of the solution
  2. additionEffervescence was observed during the addition as dissolution of the solids in the reaction
  3. customcompletion of the reaction
  4. temperaturethe reaction warmed to room temperature
  5. extractionThe mixture was extracted with Ethyl acetate
  6. dry with materialthe organic layers were dried (Mg2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c0dd5da0d6b42219cc1ee2f45a94544
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…