Sodium Bicarbonate → HCID 22989212, compound

HRID 1067547Notes

Reaction equation

HRID 1067547 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([CH:32]=[C:33]([C:35]3([C:40]([O:42][CH:43]([CH3:45])[CH3:44])=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36]3)[N:34]=2)[N:31]=1.C(=O)(O)[O-].[Na+]>>[ClH:25].[ClH:25].[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:26]3[CH:27]=[CH:28][C:29]4[N:30]([CH:32]=[C:33]([C:35]5([C:40]([O:42][CH:43]([CH3:45])[CH3:44])=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36]5)[N:34]=4)[N:31]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 22989350HCID 22989350, compound

Product 1

HCID 22989212HCID 22989212, compoundYield 116%

Procedure

1.67 g of 4-(diphenylmethoxy)-1-piperidinepropaneamine and 793 mg of isopropyl 1-(6-chloroimidazo[1,2-b]pyridazin-2-yl]cyclopentanecarboxylate were stirred at 165° C. for 5.5 hours. After cooling, aqueous sodium bicarbonate was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline and dried with magnesium sulfate. The dry product was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol:triethylamine (100:5:2). The desired fraction was collected, concentrated under reduced pressure and dissolved in 5 ml of ethyl acetate; 0.84 ml of a 4 N solution of hydrogen chloride in ethyl acetate was added, followed by concentration. The residue was powdered by the addition of ethyl ether; the resulting powder was collected by filtration, washed with ethyl ether and dried to yield 999 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saturated saline
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe dry product was concentrated under reduced pressure
  6. washeluted with ethyl acetate:methanol:triethylamine (100:5:2)
  7. customThe desired fraction was collected
  8. concentrationconcentrated under reduced pressure
  9. dissolutiondissolved in 5 ml of ethyl acetate
  10. addition0.84 ml of a 4 N solution of hydrogen chloride in ethyl acetate was added
  11. concentrationfollowed by concentration
  12. additionThe residue was powdered by the addition of ethyl ether
  13. filtrationthe resulting powder was collected by filtration
  14. washwashed with ethyl ether
  15. customdried

Sources & evidence

ORD record
ord-8bce9b0f02774c39b8503517c92c55e4
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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