Hydrochloric Acid → 3-(Isopropylamino)azetidine-3-carboxamide hydrochloride

HRID 2054396Notes

Reaction equation

HRID 2054396 reaction equation
C([N:14]1[CH2:17][C:16]([NH:21][CH:22]([CH3:24])[CH3:23])([C:18]([NH2:20])=[O:19])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:25].CCOCC.O>CO.[OH-].[OH-].[Pd+2]>[ClH:25].[CH:22]([NH:21][C:16]1([C:18]([NH2:20])=[O:19])[CH2:17][NH:14][CH2:15]1)([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 587216991-Benzhydryl-3-isopropylaminoazetidine-3-carboxylic Acid Amide

Product 1

HCID 467351463-(Isopropylamino)azetidine-3-carboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-benzhydryl-3-isopropylaminoazetidine-3-carboxylic acid amide (I-3A-1b; 2.28 g, 7.05 mmol) in methanol (100 ml) was added 1M HCl in ether (14.8 ml, 14.8 mmol) and then water (10 ml). After the addition of 20% Pd(OH)2 on carbon (60% water; 1.43 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, in vacuo. The residue was then concentrated, in vacuo, from toluene (2×), acetonitrile (2×) and then methanol to give I-3A-1c (1.59 g, 98%) as a tan solid: +APcI MS (M+1) 158.1; 1H NMR (400 MHz, CD3OD) δ 4.71 (d, J=13.3 Hz, 2H), 4.60 (d, J=13.3 Hz, 2H), 3.49 (septuplet, J=6.6 Hz, 1H), 1.34 (d, J=6.6 Hz, 6H).

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe mixture was filtered through a pad of Celite®
  4. concentrationconcentrated, in vacuo
  5. concentrationThe residue was then concentrated, in vacuo, from toluene (2×), acetonitrile (2×)
  6. custommethanol to give I-3A-1c (1.59 g, 98%) as a tan solid

Sources & evidence

ORD record
ord-a676acfbfe294daa999764848a3406f0
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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