1-Benzyl-4-(ethylamino)piperidine-4-carboxamide → 4-(Ethylamino)piperidine-4-carboxamide

HRID 2054387Notes

Reaction equation

HRID 2054387 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([NH:17][CH2:18][CH3:19])([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH2:18]([NH:17][C:11]1([C:14]([NH2:16])=[O:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH3:19]

Participants

4

Reactant 1

HCID 705671-Benzyl-4-(ethylamino)piperidine-4-carboxamide

Product 1

HCID 965734-(Ethylamino)piperidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-4-ethylaminopiperidine-4-carboxylic acid amide (I-1A-1g; 7.39 g, 28.3 mmol) in methanol (100 ml) was added 20% Pd(OH)2 on carbon (50% water; 1.48 g). The mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature overnight. The mixture was filtered through a pad of Celite®, and then concentrated to give a colorless solid I-1A-1 h (4.84 g, quantitative): +APcI MS (M+1) 172.2; 1H NMR (400 MHz, CD2Cl2) δ 2.89 (ddd, J=12.9, 8.7, 3.3 Hz, 2H), 2.75 (ddd, J=12.9, 6.6, 3.7 Hz, 2H), 2.45 (q, J=7.2 Hz, 2H), 1.95 (ddd, J=13.7, 8.3, 3.7 Hz, 2H), 1.55 (ddd, J=13.7, 6.6, 3.3 Hz, 2 h), 1.08 (t, J=7.1 Hz, 3H).

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe mixture was filtered through a pad of Celite®
  4. concentrationconcentrated
  5. customto give a colorless solid I-1A-1 h (4.84 g, quantitative)

Sources & evidence

ORD record
ord-ccda71d217094b49bf14ef75fa719904
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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