1,1-Dimethylethyl 4-(4-chlorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate → tert-Butyl 4-(4-chlorophenyl)piperidine-1-carboxylate

HRID 1487901Notes

Reaction equation

HRID 1487901 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 157514251,1-Dimethylethyl 4-(4-chlorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate2×

Product 1

HCID 27281794tert-Butyl 4-(4-chlorophenyl)piperidine-1-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Into a 250-mL round-bottom flask, was placed a mixture of Pt2O (200 mg) and methanol (50 mL). The mixture was purged with nitrogen, then hydrogen was introduced and the mixture was stirred for 15 min. A solution of tert-butyl 4-(4-chlorophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (compound 42.2, 6.00 g, 20.4 mmol) in methanol (50 mL) was added and the resulting mixture was stirred under hydrogen overnight at room temperature. After purging with nitrogen, the solids were filtered off and the resulting solution was concentrated under vacuum to yield the title compound as a light green oil (5.30 g, 88%).

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. customThe mixture was purged with nitrogen
  3. additionhydrogen was introduced
  4. stirringthe resulting mixture was stirred under hydrogen overnight at room temperature
  5. customAfter purging with nitrogen
  6. filtrationthe solids were filtered off
  7. concentrationthe resulting solution was concentrated under vacuum

Sources & evidence

ORD record
ord-b9bb40305bda42ae8f2410a87dcf3fe5
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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