Formaldehyde → HCID 69666069, compound

HRID 2211871Notes

Reaction equation

HRID 2211871 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH2:24])[CH2:12][CH2:11]2)=[N:2]1.[Na].[CH2:26]=[O:27]>CO.O>[OH-:27].[NH4+:2].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][CH3:26])[CH2:12][CH2:11]2)=[N:2]1

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5360545SodiumHCID 21963169HCID 21963169, compound

Product 2

HCID 14923Ammonium HydroxideHCID 69666069HCID 69666069, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

2-[2-(4-1,2-Benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine (6.76 g, 20.0 mmol) was added to a suspension of sodium metal (2.3 g, 100 mmol) in methanol (30 mL) at rt. The resulting solution was then added to a suspension of paraformaldehyde (0.84 g) in methanol (20 mL). Suspension was warmed to reflux for 4 h. Reaction was cooled to room temperature followed by a careful quench with water (100 mL) and concentration of resulting suspension. The crude was diluted with water (100 mL) and extracted with methylene chloride (150 mL). The extract was dried over magnesium sulfate, filtered and concentrated to brown oil. The crude mixture was purified via medium pressure liquid chromatography using a 300 g silica gel Biotage cartridge eluting with a gradient of methylene chloride to (100:8:1) methylene choride: ethanol: ammonium hydroxide to yield pure {2-[2-(4-1,2-benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-methyl-amine as an oil (3.73 g). Yield 53%;

Workup

  1. temperatureSuspension was warmed
  2. temperatureto reflux for 4 h
  3. customReaction
  4. customa careful quench with water (100 mL) and concentration
  5. customof resulting suspension
  6. extractionextracted with methylene chloride (150 mL)
  7. dry with materialThe extract was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to brown oil
  10. customThe crude mixture was purified via medium pressure liquid chromatography
  11. washeluting with a gradient of methylene chloride to (100:8:1) methylene choride

Sources & evidence

ORD record
ord-9ccf986f10f346a28e0fb4319c9b0b95
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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