Hydrochloric Acid → 1246249-82-0

HRID 591654Notes

Reaction equation

HRID 591654 reaction equation
[CH:1]([N:4]([CH:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)[C:5](=[O:7])[CH3:6])([CH3:3])[CH3:2].[ClH:21]>>[ClH:21].[CH:1]([N:4]([CH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[C:5](=[O:7])[CH3:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 66745169HCID 66745169, compound

Product 1

HCID 532558691246249-82-0Yield 45%

Procedure

A solution of tert-butyl 4-(N-isopropylacetamido)piperidine-1-carboxylate (0.880 g, 3.09 mmol) in hydrogen chloride (4.0 M solution in 1,4-dioxane, 10 mL) was stirred at room temperature overnight. The resulting solution was concentrated in vacuo, basified with aqueous saturated NaHCO3, and extracted with EtOAc. The organics were dried (Na2SO4), filtered, and concentrated in vacuo. The material was purified by flash chromatography on silica gel, eluting with 50% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2. The residue was further purified by flash chromatography on silica gel, eluting with 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH, to afford N-Isopropyl-N-(piperidin-4-yl)acetamide hydrogen chloride (0.260 g, 45%) as a clear liquid.

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. dry with materialThe organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe material was purified by flash chromatography on silica gel
  7. washeluting with 50% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2
  8. customThe residue was further purified by flash chromatography on silica gel
  9. washeluting with 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH

Sources & evidence

ORD record
ord-af57b132eb3f4857ac2b63f5507a3723
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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