Methyl iodide → HCID 18008655, compound

HRID 990577Notes

Reaction equation

HRID 990577 reaction equation
[C:1]1([C:7]2([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][I:20]>CO>[I-:20].[CH3:19][N+:13]1([CH2:12][C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 566548Piperidine, 1-((-phenylcyclopentyl)methyl)-

Product 1

HCID 18008655HCID 18008655, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mechanically stirred solution of [(1-phenylcyclopentyl)methyl]piperidine (115 gm; 0.47 mole) in 1000 ml methanol (ACS reagent), methyl iodide (100 gm; 0.7 mole) were added. The resulting mixture was stirred for 48 hrs. Then an additional 35 gm (0.5 mole equivalent) of methyl iodide was added and the reaction was heated for 1 hr. The resulting solution was concentrated under reduced pressure on a rotary evaporator to give 175 gm of a tan solid material. The obtained solid was re-crystallized by dissolving in hot isopropyl alcohol and allowed to re-crystallize overnight. Re-crystallization afforded 171 gm of the product (NMR analysis) as shinny white needles.

Workup

  1. temperaturethe reaction was heated for 1 hr
  2. concentrationThe resulting solution was concentrated under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-8fa7999e1deb4a8fa41ede6168b6b113
Source dataset
uspto-grants-2002_10
Patent number
US06461578B1

Reaction notes

Loading…