Potassium Carbonate → 3-Cyclopentyl-propyl (2,2-dimethoxy-ethyl)-amine

HRID 1004639Notes

Reaction equation

HRID 1004639 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C(=O)([O-])[O-].[K+].[K+].[CH:14]1([CH2:19][CH2:20][CH2:21]I)[CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C)C=O>[CH:14]1([CH2:19][CH2:20][CH2:21][NH:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 89728Aminoacetaldehyde dimethyl acetalHCID 15508337(3-Iodopropyl)cyclopentane

Product 1

HCID 187930233-Cyclopentyl-propyl (2,2-dimethoxy-ethyl)-amineYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-aminoacetaldehyde dimethyl acetal (3.0 mL, 27.5 mmol), solid potassium carbonate (2.1 g, 15.2 mmol), and 3-cyclopentyl-1-iodopropane (3.3 g, 13.9 mmol) in anhydrous N,N-dimethylformamide was stirred for 12 hours at room temperature. The mixture was filtered, and the filtrate was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and concentrated to a crude oil. The crude was passed through a plug of silica gel with ethyl acetate to provide a yellow oil (2.67 g, 89%). H NMR (300 MHz, DMSO-d6) δ 4.35 (t, 1 H), 3.23 (s, 6 H), 2.54 (d, 2 H), 1.70 (m, 3 H), 1.51 (m, 6 H), 1.36 (m, 2 H), 1.27 (m, 2 H), 1.04 (m, 2 H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a crude oil

Sources & evidence

ORD record
ord-dc1868b2c9ba41589a832f8ff89849b3
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

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