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

HRID 1071165Notes

Reaction equation

HRID 1071165 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%). 1H NMR (300 MHz, DMSO-d6) δ 4.35 (t, 1H), 3.23 (s, 6H), 2.54 (d, 2H), 1.70 (m, 3H), 1.51 (m, 6H), 1.36 (m, 2H), 1.27 (m, 2H), 1.04 (m, 2H).

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-bdc9be844bf34f4ebf1074f08834c5f6
Source dataset
uspto-grants-2005_06
Patent number
US06903218B2

Reaction notes

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