1-Benzhydryl-3-(benzylethylamino)-azetidine-3-carboxylic acid amide hydrochloride salt → 3-(Ethylamino)piperidine-3-carboxamide hydrochloride

HRID 348005Notes

Reaction equation

HRID 348005 reaction equation
[ClH:1].[CH:2]([N:15]1[CH2:18][C:17]([NH:22][CH2:23][CH2:24]CC2C=CC=CC=2)([C:19]([NH2:21])=[O:20])[CH2:16]1)([C:9]1C=CC=CC=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[ClH:1].[CH2:23]([NH:22][C:17]1([C:19]([NH2:21])=[O:20])[CH2:16][CH2:9][CH2:2][NH:15][CH2:18]1)[CH3:24]

Participants

4

Reactant 1

HCID 692135481-Benzhydryl-3-(benzylethylamino)-azetidine-3-carboxylic acid amide hydrochloride salt

Product 1

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

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 1-benzhydryl-3-(benzylethylamino)-azetidine-3-carboxylic acid amide hydrochloride salt (I-1A-3c; 0.66 g, 1.4 mmol) in methanol (25 ml) was added 20% Pd(OH)2 on carbon (30% water; 0.13 g). The mixture was placed on a Parr® shaker and then reduced (45 psi H2) at room temperature overnight. The mixture was diluted with methanol (200 ml) filtered through a 0.45 μm filter disk, and then concentrated to a solid. The residue was triturated from diethyl ether, collected by vacuum filtration, washed with ether and then dried, in vacuo, to afford I-1A-3e (298 mg, 98%): +APcI MS (M+1) 144.1; 1H NMR (400 MHz, CD2Cl2) δ 4.56 (br s, 4H), 3.00 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.1 Hz, 3H).

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationfiltered through a 0.45 μm
  4. filtrationfilter disk
  5. concentrationconcentrated to a solid
  6. customThe residue was triturated from diethyl ether
  7. filtrationcollected by vacuum filtration
  8. washwashed with ether
  9. customdried, in vacuo
  10. customto afford I-1A-3e (298 mg, 98%)

Sources & evidence

ORD record
ord-c2c657193b4d44c1b5a434802fe8dc85
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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