Sodium Iodide → HCID 67827581, compound

HRID 1109534Notes

Reaction equation

HRID 1109534 reaction equation
C(NC(C1C=CC2SC3C(=CC=CC=3)N([CH:21]([N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:22][CH3:23])C=2C=1)=O)CC.[CH:29]1(CBr)[CH2:31][CH2:30]1.[C:34](=O)([O-])[O-].[Na+].[Na+].[I-:40].[Na+]>CC(C)=O.CN(C)C=O>[I-:40].[CH:22]1([CH2:21][N+:24]2([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:23][CH2:34]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81503BromomethylcyclopropaneHCID 19020502HCID 19020502, compound

Product 1

HCID 67827581HCID 67827581, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of N-propyl-10-[1-(1-pyrrolidinyl)-propyl]-2-phenothiazinecarboxamide, L series (0.6 g), cyclopropylmethyl bromide (0.74 cc), sodium carbonate (1 g) and sodium iodide (0.5 g) in a mixture of acetone (25 cc) and dimethylformamide (0.5 cc) is brought to reflux with stirring for 40 hours, cooled and filtered, and the filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 55°-60° C. The orange-colored oily residue (1.98 g) is taken up with stirring with isopropyl ether (35 cc) for 16 hours at a temperature in the region of 20° C. The suspension obtained is filtered and the solid is drained, washed with isopropyl ether (2×10 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 37° C. This yellow solid (1.25 g) is taken in dichloromethane (12 cc) with stirring for 2 hours and the suspension obtained is filtered. The filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and the orange-colored oily residue (0.69 g) is solidified by stirring for one hour in diethyl ether (30 cc). The solid formed is separated by filtration, washed with diethyl ether (2×5 cc), drained and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 37° C. 1-Cyclopropylmethyl-1-[2-propyl]pyrrolidinium iodide, L series (0.59 g), is thereby obtained in the form of an orange-yellow solid, m.p. about 125°-130° C.

Workup

  1. temperatureto reflux
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 55°-60° C
  5. stirringwith stirring with isopropyl ether (35 cc) for 16 hours at a temperature in the region of 20° C
  6. customThe suspension obtained
  7. filtrationis filtered
  8. washwashed with isopropyl ether (2×10 cc)
  9. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 37° C
  10. stirringwith stirring for 2 hours
  11. customthe suspension obtained
  12. filtrationis filtered
  13. concentrationThe filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  14. stirringby stirring for one hour in diethyl ether (30 cc)
  15. customThe solid formed
  16. customis separated by filtration
  17. washwashed with diethyl ether (2×5 cc)
  18. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 37° C

Sources & evidence

ORD record
ord-b72188a5da7e44f48958b24a95142f2a
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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