Hydrochloric Acid → 1-(3-Methylazetidin-3-yl)pyrrolidine;dihydrochloride

HRID 1366579Notes

Reaction equation

HRID 1366579 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][C:10]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)([CH3:12])[CH2:9]2)C=CC=CC=1.[ClH:24]>C(O)C.[OH-].[OH-].[Pd+2]>[ClH:24].[ClH:24].[CH3:12][C:10]1([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:11][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 669361071-[1-(Diphenylmethyl)-3-methyl-3-azetidinyl]pyrrolidine

Product 1

HCID 669364881-(3-Methylazetidin-3-yl)pyrrolidine;dihydrochlorideYield 86%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-[1-(diphenylmethyl)-3-methyl-3-azetidinyl]pyrrolidine (0.94 g, 3.07 mmol) and 20% Pd(OH)2 (0.11 g) in ethanol (30 ml) and 1N HCl (7 ml) was treated with H2 at 60 psi overnight. The catalyst was removed by filtration, and the filtrate was evaporated under vacuum. The residue was washed with benzene (3×5 ml) and dried under high vacuum to provide 1-(3-methyl-3-azetidinyl)pyrrolidine dihydrochloride (0.76 g, presumed 86% pure). LCMS: (M+H)+: 141.0.

Workup

  1. additionwas treated with H2 at 60 psi overnight
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated under vacuum
  4. washThe residue was washed with benzene (3×5 ml)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-f50d1544b4f746e19953e0e1766bcd5c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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