Hydrochloric Acid → 3-(Ethylamino)piperidine-3-carboxamide hydrochloride

HRID 348006Notes

Reaction equation

HRID 348006 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([NH:21][CH2:22][CH3:23])([C:18]([NH2:20])=[O:19])[CH2:15]1)([C:8]1C=CC=CC=1)C1C=CC=CC=1.[ClH:24]>CO.CC(OC)(C)C.[OH-].[OH-].[Pd+2]>[ClH:24].[CH2:22]([NH:21][C:16]1([C:18]([NH2:20])=[O:19])[CH2:15][CH2:8][CH2:1][NH:14][CH2:17]1)[CH3:23]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 587217631-Benzhydryl-3-ethylaminoazetidine-3-carboxylic Acid Amide

Product 1

HCID 1317262483-(Ethylamino)piperidine-3-carboxamide hydrochloride

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a suspension of 1-benzhydryl-3-ethylaminoazetidine-3-carboxylic acid amide (I-1A-3d; 36.1 g, 117 mmol) in methanol (560 ml) at room temperature was added concentrated aqueous HCl (19.5 ml, 234 mmol), resulting in a clear solution. To 20% Pd(OH)2 on carbon (3.75 g) was added methanol (85 ml), followed by the methanolic solution of I-1A-3d. The mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature for 20 hours. The reaction was then filtered through Celite® and then concentrated to low volume under reduced pressure, at which point a precipitate formed. The suspension was diluted with MTBE (500 ml), stirred for an additional hour, and the precipitate collected by vacuum filtration. The solid was washed with MTBE and then dried, in vacuo, to afford I-1A-3e (24.8 g, 98%) as a colorless solid.

Workup

  1. customresulting in a clear solution
  2. customat room temperature
  3. customfor 20 hours
  4. filtrationThe reaction was then filtered through Celite®
  5. concentrationconcentrated to low volume under reduced pressure, at which point a precipitate
  6. customformed
  7. filtrationthe precipitate collected by vacuum filtration
  8. washThe solid was washed with MTBE
  9. customdried, in vacuo
  10. customto afford I-1A-3e (24.8 g, 98%) as a colorless solid

Sources & evidence

ORD record
ord-390d15ce2ec946e18b7670d3d584086b
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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