HCID 66799123, compound → HCID 66799294, compound

HRID 1193324Notes

Reaction equation

HRID 1193324 reaction equation
COC1C=CC([CH2:7][N:8](C)[CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[CH2:11][C:10]2([CH3:22])[CH3:21])=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:7][NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[CH2:11][C:10]1([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 66799123HCID 66799123, compound

Product 1

HCID 66799294HCID 66799294, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(4-methoxybenzyl)-N,3,3-trimethyl-1-(pyridin-4-yl)piperidin-4-amine (320 mg, 0.944 mmol, 1 eq) in MeOH (6 ml) was degassed for 15 min with nitrogen, then Pd(OH)2 (320 mg) was added and hydrogenation was carried out for 5 h at RT under balloon pressure (H2). After monitoring by thin-layer chromatography, the reaction mixture was filtered off over Celite and the filtrate was concentrated under reduced pressure. The crude product so obtained was used in the next stage without being purified further. Yield: 92% (190 mg, 0.867 mmol).

Workup

  1. filtrationthe reaction mixture was filtered off over Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ceaaa90f933e45d19cba122f51040ee0
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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