Hydrochloric Acid → 1-(1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methylamine

HRID 10352Notes

Reaction equation

HRID 10352 reaction equation
O.NN.[CH2:4]([N:11]1[CH2:15][CH2:14][C:13]([CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)([CH2:16][O:17][CH3:18])[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C(O)C>[CH2:4]([N:11]1[CH2:15][CH2:14][C:13]([CH2:19][NH2:20])([CH2:16][O:17][CH3:18])[CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 578326372-(1-Benzyl-3-methoxymethylpyrrolidin-3-ylmethyl)isoindole-1,3-dione

Product 1

HCID 219789711-(1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methylamineYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (85% solution in water, 0.372 g, 6.32 mmol) is added to a solution of 2-(1-benzyl-3-methoxymethylpyrrolidin-3-ylmethyl)isoindole-1,3-dione (Example A20, 1.581 g, 4.34 mmol) in ethanol (50 mL). The resulting mixture is refluxed for 4.5 hours, cooled and acidified with concentrated hydrochloric acid. The precipitate is removed by filtration and the filtrate is concentrated in vacuo. The residue is dissolved in ethanol/water (2:1) and the insoluble material is removed by filtration. The filtrate is basified to pH 10 with 1N sodium hydroxide solution and extracted with dichloromethane. The combined organic extracts are dried over Na2SO4, filtered and concentrated under vacuum to afford the title compound (0.910 g). 1H NMR (200 MHz, CDCl3): δ 7.41–7.15 (m, 5H), 3.57 (s, 2H), 3.33 (s, 3H), 3.30 (s, 2H), 2.71 (s, 2H), 2.64–2.51 (m, 2H), 2.42–2.24 (m, 2H), 1.68–1.52 (m, 2H), 1.38–1.10 (m, 2H).

Workup

  1. temperatureThe resulting mixture is refluxed for 4.5 hours
  2. temperaturecooled
  3. customThe precipitate is removed by filtration
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved in ethanol/water (2:1)
  6. customthe insoluble material is removed by filtration
  7. extractionextracted with dichloromethane
  8. dry with materialThe combined organic extracts are dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bb473ca2021b44e6ad238522ab891e1c
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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