Cyclopentylamine → N-(2,2-dimethoxyethyl)cyclopentanamine

HRID 909877Notes

Reaction equation

HRID 909877 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH:10]=O>CO.O.[Pd]>[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10][NH:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 2906CyclopentylamineHCID 162650Acetaldehyde, 2,2-dimethoxy-

Product 1

HCID 58168622N-(2,2-dimethoxyethyl)cyclopentanamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of cyclopentanamine (5 g) in methanol (20 mL) was added 2,2-dimethoxyacetaldehyde 60% in water (8.86 mL) and the mixture stirred at ambient temperature for 5 h. A slurry of palladium on carbon (10%, 200 mg) in methanol (5 mL) was added and the mixture hydrogenated at 5 bar for 16 h. It was filtered and concentrated in vacuo to afford N-(2,2-dimethoxyethyl)cyclopentanamine (9.44 g) as a oil. 1H NMR (400 MHz, CDCl3) δ 4.47 (t, J=5.6 Hz, 1H), 3.39 (s, 6H), 3.05 (quintet, J=6.8 Hz, 1H), 2.72 (d, J=5.4 Hz, 2H), 1.89-1.80 (m, 2H), 1.73-1.62 (m, 2H), 1.58-1.48 (m, 2H), 1.36-1.27 (m, 2H)

Workup

  1. waitthe mixture hydrogenated at 5 bar for 16 h
  2. filtrationIt was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44df8fe503834fb9bf3ae2f107582848
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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