Hydrochloric Acid → HCID 22291216, compound

HRID 1592300Notes

Reaction equation

HRID 1592300 reaction equation
[ClH:1].C([N:9]1[C:13]2([CH2:17][CH2:16][N:15]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:14]2)[CH2:12][CH2:11][CH2:10]1)C1C=CC=CC=1>[Pd].CO>[ClH:1].[ClH:1].[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([N:15]2[CH2:16][CH2:17][C:13]3([NH:9][CH2:10][CH2:11][CH2:12]3)[CH2:14]2)[CH:19]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 222911891-Benzyl-7-(pyridin-3-yl)-1,7-diazaspiro[4.4]nonane

Product 1

HCID 22291216HCID 22291216, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Aqueous hydrochloric acid (0.5 mL of 12 M) and 10% palladium on carbon (0.100 g) were added to a solution of 1-benzyl-7-(3-pyridyl)-1,7-diazaspiro[4.4]nonane (1.0 g, 3.41 mmol) in methanol (30 mL). The mixture was shaken under a hydrogen atmosphere (50 psi) in a Parr hydrogenation apparatus for 24 h and filtered through Celite. The filtrate was concentrated by rotary evaporation and column chromatographed on Merck silica gel 60 (70-230 mesh). Elution with 0.01:1:9 (v/v) aqueous ammonia/methanol/chloroform, and concentration of selected fractions, gave 0.650 g (93.8%) of viscous, brown oil. A portion (300 mg, 1.48 mmol) of this material was treated with aqueous hydrochloric acid (2 mL). The water was azeotropically removed by repeated treatment with small volumes of ethanol (˜5 mL) and rotary evaporation. The resulting solid was recrystallized from hot isopropanol to give 360 mg (88.2%) of fine tan crystals.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated by rotary evaporation and column
  3. customchromatographed on Merck silica gel 60 (70-230 mesh)
  4. washElution with 0.01:1:9 (v/v) aqueous ammonia/methanol/chloroform, and concentration of selected fractions
  5. customgave 0.650 g (93.8%) of viscous, brown oil
  6. customThe water was azeotropically removed
  7. customwith small volumes of ethanol (˜5 mL) and rotary evaporation
  8. customThe resulting solid was recrystallized from hot isopropanol

Sources & evidence

ORD record
ord-6ff5664718c14908ba26006aa15a7534
Source dataset
uspto-grants-2007_11
Patent number
US07291731B2

Reaction notes

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