HCID 59321452, compound → Tert-butyl 4-(aminomethyl)-4-(2,3-dichlorophenyl)piperidine-1-carboxylate

HRID 1800825Notes

Reaction equation

HRID 1800825 reaction equation
[C:1]([C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[Cl:23])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].[H][H]>N.CO.[Ni]>[NH2:2][CH2:1][C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[Cl:23])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

6

Reactant 2

HCID 59321452HCID 59321452, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59321370Tert-butyl 4-(aminomethyl)-4-(2,3-dichlorophenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

Tert-butyl 4-cyano-4-(2,3-dichlorophenyl)piperidine-1-carboxylate (2.30 g, 6.47 mmol) was dissolved in 75 ml of a 7M solution of NH3 in MeOH. Raney Nickel (˜2 g aq. suspension) was added and the mixture shaken on a PARR apparatus under 60 psi of hydrogen for 4 days. The catalyst was removed by filtration through a layer of Celite and the crude reaction mixture concentrated. The crude product (1.90 g yellow oil) was used in the next reaction (amide bond formation) “as is”.

Workup

  1. customThe catalyst was removed by filtration through a layer of Celite
  2. customthe crude reaction mixture
  3. concentrationconcentrated
  4. customThe crude product (1.90 g yellow oil) was used in the next reaction (amide bond formation) “

Sources & evidence

ORD record
ord-c74be3264331470aaac52b37e03979e6
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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