Sodium Hydroxide → 3-(1-Methylpyrrolidin-2-yl)pyridine

HRID 335486Notes

Reaction equation

HRID 335486 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7](=O)[C:8]2[CH:13]=[CH:12][CH:11]=[N:10][CH:9]=2)C1=O.[OH-].[Na+].[BH4-].[K+]>Cl>[N:10]1[CH:9]=[C:8]([CH:7]2[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4069086(R,S)-1-METHYL-3-NICOTINOYLPYRROLIDONEHCID 4192641Potassium borohydride

Product 1

HCID 9423-(1-Methylpyrrolidin-2-yl)pyridineYield 75.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
135 °C

Procedure

1-methyl-3-nicotinoyl-2-pyrrolidone (20.4 g, 0.1 mol) was dissolved in a 6N hydrochloric acid (150 mL) The solution was heated to 135° C. to react for 8 h and then cooled to room temperature. The pH of the mixture was adjusted to 7 by using NaOH under an ice bath, and then potassium borohydride (5.3 g, 0.1 mol) was added therein and the temperature was back to room temperature for 2 h. 200 mL distilled water was added and the mixture was stream-distilled. The distilled water phase was concentrated till dry to give 12.2 g racemic nicotine. HPLC purity 98.4%; 1H NMR (CDCl3, 300 MHz) δ: 8.52 (d, 1H), 8.48 (dd, 1H), 7.69 (dt, 1H), 7.25 (dd, 1H), 3.23 (t, 1H), 3.07 (t, 1H), 2.29 (m, 1H), 2.16 (s, 3H), 1.90-2.04 (m, 2H), 1.65-1.88 (m, 2H), ESI-MS 163.4 (M+H).

Workup

  1. customto react for 8 h
  2. temperaturecooled to room temperature
  3. distillation200 mL distilled water
  4. additionwas added
  5. distillationthe mixture was stream-distilled
  6. concentrationThe distilled water phase was concentrated
  7. customtill dry

Sources & evidence

ORD record
ord-8cf3d1a8268940ff82e4bed17031ae62
Source dataset
uspto-grants-2014_11
Patent number
US08884021B2

Reaction notes

Loading…