1-Iodopropane → HCID 13851345, compound

HRID 979162Notes

Reaction equation

HRID 979162 reaction equation
[CH2:1]1[C@@H:6]2[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[O:9][CH2:10][C@@H:5]2[CH2:4][CH2:3][NH:2]1.I[CH2:16][CH2:17][CH3:18].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH2:16]([N:2]1[CH2:3][CH2:4][C@H:5]2[CH2:10][O:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[C@H:6]2[CH2:1]1)[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 516892Sodium BicarbonateHCID 13851343HCID 13851343, compound

Product 1

HCID 13851345HCID 13851345, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.235 g (±)-[4aR*,10bS*]-1,3,4,4a,5,10b-hexahydro-2H-[1]benzopyrano[4,3-c]pyridine in 5 ml toluene is refluxed with 200 mg iodopropane and 3 ml saturated NaHCO3 solution for 2 hours. The organic phase is separated, dried over Na2SO4, filtered, concentrated in vacuo, and flash chromatographed with CH2Cl2 /ammonia saturated methanol (95:5)to give the title compound; m.p. HCl salt 245°-247°.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo, and flash
  5. customchromatographed with CH2Cl2 /ammonia saturated methanol (95:5)to

Sources & evidence

ORD record
ord-bce7911e51eb4a8c984214c1f7f9f937
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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