Hydrochloric Acid → 3-Azetidinecarboxamide, 3-(methylamino)-, hydrochloride (1:1)

HRID 915847Notes

Reaction equation

HRID 915847 reaction equation
C([N:14]1[CH2:17][C:16]([NH:21][CH3:22])([C:18]([NH2:20])=[O:19])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:23]>CO.[OH-].[OH-].[Pd+2]>[ClH:23].[CH3:22][NH:21][C:16]1([C:18]([NH2:20])=[O:19])[CH2:17][NH:14][CH2:15]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58721711HCID 58721711, compound

Product 1

HCID 1317262493-Azetidinecarboxamide, 3-(methylamino)-, hydrochloride (1:1)

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 1-benzhydryl-3-methylaminoazetidine-3-carboxylic acid amide (I-2A-69b; 13.5 g, 45.8 mmol) in methanol (90 ml) was added concentrated aqueous HCl (8.0 ml, 96 mol), dropwise, to give a homogeneous solution. After the addition of 20% Pd(OH)2 on carbon (50% water; 4.1 g), the mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature for 7 hours. The mixture was filtered through a pad of Celite®, washing with a copious amount of 9:1 methanol/water, and then 9:1 tetrahydrofuran/water until no product eluted (determined with ninhydrin stain). The filtrate was then concentrated, in vacuo, and the residue was then triturated from diethyl ether to give I-2A-90a (9.3 g, quantitative) as a brown solid: +APcl MS (M+1) 129.9; 1H NMR (400 MHz, CD3OD) δ 4.50 (d, J=12.0 Hz, 2H), 4.43 (d, J=12.9 Hz, 2H), 2.64 (s, 3H).

Workup

  1. customdropwise, to give a homogeneous solution
  2. customat room temperature
  3. customfor 7 hours
  4. filtrationThe mixture was filtered through a pad of Celite®
  5. washwashing with a copious amount of 9:1 methanol/water
  6. wash9:1 tetrahydrofuran/water until no product eluted (determined with ninhydrin stain)
  7. concentrationThe filtrate was then concentrated, in vacuo
  8. customthe residue was then triturated from diethyl ether
  9. customto give I-2A-90a (9.3 g, quantitative) as a brown solid

Sources & evidence

ORD record
ord-83195cec079946f0b0ee41ce10e81ec3
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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