Hydrogen chloride-ethyl acetate → Tert-butyl 4-[2-(piperidin-4-yl)ethyl]piperidine-1-carboxylate hydrochloride

HRID 2074339Notes

Reaction equation

HRID 2074339 reaction equation
[ClH:1].CCOC(C)=O.[N:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:10][CH:9]=1.[H][H]>[Pt]=O.C(O)C>[ClH:1].[NH:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21]2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57450068tert-butyl 4-[(E)-2-pyridin-4-ylvinyl]piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57421848Tert-butyl 4-[2-(piperidin-4-yl)ethyl]piperidine-1-carboxylate hydrochloride

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A 4 M hydrogen chloride/EtOAc solution (0.88 ml) and platinum oxide (100 mg) were added to an ethanol (25 ml) solution of tert-butyl 4-[(E)-2-pyridin-4-ylvinyl]piperidine-1-carboxylate (1.02 g), followed by stirring in the presence of hydrogen (3.5 atm) for 24 hours. This was purged with argon, diluted with methanol, filtered through Celite, and concentrated under reduced pressure. The solid precipitated was washed with EtOAc/hexane, and dried under reduced pressure to obtain tert-butyl 4-(2-piperidin-4-ylethyl)piperidine-1-carboxylate hydrochloride (850 mg) as a white solid.

Workup

  1. customThis was purged with argon
  2. additiondiluted with methanol
  3. filtrationfiltered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe solid precipitated
  6. washwas washed with EtOAc/hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-d9f242b156a54f4199e95d3dd104d207
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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