Hydrochloric Acid → 4-Amino-1-ethanesulfonylpiperidine

HRID 2069086Notes

Reaction equation

HRID 2069086 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OCC2C=CC=CC=2)[CH2:10][CH2:9]1.[CH2:25]([S:27](Cl)(=[O:29])=[O:28])[CH3:26].Cl>ClCCl>[CH2:25]([S:27]([N:8]1[CH2:9][CH2:10][CH:11]([NH2:14])[CH2:12][CH2:13]1)(=[O:29])=[O:28])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 15143044-Cbz-aminopiperidine

Product 1

HCID 167761864-Amino-1-ethanesulfonylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (10 mL) was added to a dichloromethane (90 mL) solution of Benzyl piperidin-4-ylcarbamate (5.09 g) at 0° C. followed by the dropwise addition of ethane sulfonylchloride (which may be referred to as sso10; 3.2 mL; TCI) and the resulting mixture was stirred overnight slowly raising to room temperature. 1 N Hydrochloric acid (90 mL; WAKO) was added to the reaction mixture solution, the resulting mixture was stirred for approx. 10 minutes, then the reaction mixture was extracted with chloroform, the organic layer was dried, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen; chloroform/methanol). Palladium hydroxide (20% by weight, Wet-type, 5 g; NECHEM) was added to a methanol (90 mL) solution of this product under a nitrogen atmosphere. The atmosphere in a reaction vessel was replaced with hydrogen at room temperature, the resulting mixture was stirred overnight, the atmosphere in the reaction vessel was returned to a nitrogen atmosphere, the residue was removed by filtration, the solvent was evaporated under reduced pressure, and the residue was dried to give the title compound (3.32 g).

Workup

  1. stirringthe resulting mixture was stirred for approx. 10 minutes
  2. extractionthe reaction mixture was extracted with chloroform
  3. customthe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (Yamazen; chloroform/methanol)
  6. additionPalladium hydroxide (20% by weight, Wet-type, 5 g; NECHEM) was added to a methanol (90 mL) solution of this product under a nitrogen atmosphere
  7. customThe atmosphere in a reaction vessel was replaced with hydrogen at room temperature
  8. stirringthe resulting mixture was stirred overnight
  9. customthe residue was removed by filtration
  10. customthe solvent was evaporated under reduced pressure
  11. customthe residue was dried

Sources & evidence

ORD record
ord-59304903a3b547e281235a3a0c7c285f
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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