Hydrochloric Acid → 4-(4-Ethynylphenyl)piperidine hydrochloride

HRID 1487942Notes

Reaction equation

HRID 1487942 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[CH:2].[ClH:22]>C(OCC)(=O)C>[ClH:22].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:5][CH:4]=1)#[CH:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59805226Tert-butyl 4-(4-ethynylphenyl)piperidine-1-carboxylate2×

Product 1

HCID 900215424-(4-Ethynylphenyl)piperidine hydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of tert-butyl 4-(4-ethynylphenyl)piperidine-1-carboxylate (compound 76.3, 1.0 g, 3.5 mmol) in ethyl acetate (20 mL). Hydrogen chloride (g) was introduced by bubbling through the solution and the resulting solution was stirred for 1 hour at room temperature. The solids that formed were collected by filtration and washed with hexanes (3×10 mL) to yield the title compound as a brown solid (630 mg, 81%).

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customby bubbling through the solution
  3. customThe solids that formed
  4. filtrationwere collected by filtration
  5. washwashed with hexanes (3×10 mL)

Sources & evidence

ORD record
ord-d5de80c660224614bf28650af0562e4a
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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