HCID 178484110, compound → HCID 178484106, compound

HRID 1169414Notes

Reaction equation

HRID 1169414 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][N:19]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH3:20])[CH2:14][CH2:13]1)=O)C1C=CC=CC=1>[Pd].C(O)C>[NH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][N:19]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH3:20])[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 178484110HCID 178484110, compound

Product 1

HCID 178484106HCID 178484106, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl trans-4-[N-[4-(N-benzyloxycarbonylamino)cyclohexylmethyl]-N-methylamino]piperidine-1-carboxylate (4.5 g), Pd-C (0.43 g) and ethanol (300 ml) was stirred vigorously for 24 hours under a hydrogen atmosphere. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The precipitated crystals were collected by filtration. The crystals were washed with diethyl ether to obtain tert-butyl trans-4-[N-(4-aminocyclohexylmethyl)-N-methylamino]piperidine-1-carboxylate (2.80 g) as colorless crystals.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationThe precipitated crystals were collected by filtration
  4. washThe crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-ca29f4b762aa4b8ab1da11500937337a
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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