Methanol → alpha-Nicotine

HRID 749057Notes

Reaction equation

HRID 749057 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:20]=[CH:19][C:18]2OC3C(=CC=CC=3)NC=2C=1.[NH2:21][CH2:22]CC1CCCN1C.[Cl-].[Al+3].[Cl-].[Cl-].CO>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:20][CH2:19][CH2:18][N:21]1[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 6451240Aluminum(III) ChlorideHCID 68901151HCID 68901151, compound

Product 1

HCID 212128alpha-NicotineYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Pyridinyl phenoxazine (28 mg,), 2-(2-aminoethyl)-1-methylpyrrolidine (17 ul, 0.1173 mmol) and aluminum chloride (21 mg, 0.1575 mmol) were mixed in anhydrous dichloromethane (1 ml) and stirred for 1 h. The mixture was then evaporated to a residue which was washed with saturated aqueous sodium potassium tartaric acid. The mixture was then extracted with 3×10 ml dichloromethane and the extracts dried (Na2SO4) and evaporated. The compound was then isolated using preparative thin layer chromatography (Al2O3, 3% MeOH in dichloromethane) to yield the 2-pyridinyl methylpyrrolidine (17.5 mg) as a yellow solid.

Workup

  1. customThe mixture was then evaporated to a residue which
  2. washwas washed with saturated aqueous sodium potassium tartaric acid
  3. extractionThe mixture was then extracted with 3×10 ml dichloromethane
  4. dry with materialthe extracts dried (Na2SO4)
  5. customevaporated
  6. customThe compound was then isolated

Sources & evidence

ORD record
ord-56f3d1f0b8b84474aa32b4edf416d593
Source dataset
uspto-grants-2008_07
Patent number
US07402579B2

Reaction notes

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