Pyridine → HCID 9324935, compound

HRID 645467Notes

Reaction equation

HRID 645467 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[CH3:11][O:12][CH2:13][C:14](Cl)=[O:15].N1C=CC=CC=1>CN(C=O)C>[CH3:11][O:12][CH2:13][C:14]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2)=[O:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 90496Indan-5-amineHCID 96623Methoxyacetyl chloride

Product 1

HCID 9324935HCID 9324935, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-aminoindan (4.66 g, 35.0 mmol) in anhydrous DMF (26 ml) was slowly added methoxyacetyl chloride (5.70 g, 52.50 mmol) followed by pyridine (8.5 ml, 105.0 mmol). The red solution was stirred at room temperature for 3.5 hours under argon, then it was partitioned between ethyl acetate (200 ml) and 1N HCl (120 ml). The organic layer was washed with more 1N HCl (120 ml), brine (100 ml), dried (Na2SO4) and concentrated in vacuo. The residue was triturated with diethyl ether; the white precipitate was collected by filtration, washed with diethyl ether to afford the title compound (5.93 g, 83%), m.p. 104-105° C.; 1H-NMR (250 MHz, CDCl3, TMS) 2.06 (m, 2H, 2-CH2), 2.87 (m, 4H, 1-CH2 and 3-CH2), 3.50 (s, 3H, OCH3), 4.00 (s, 2H, 2≧CH2OMe), 7.22 (m (overlap with CHCl3 peak), 2H, 6-H, 7-H), 7.52 (s, 1H, 4-H), 8.18 (s, 1H, CONH); MS (ESI, m/z): 432 [(2M+Na)+, 30%], 206 [(M+H)+, 100%]; Found C, 70.10; H, 7.38; N, 6.81. C12H15NO2 requires C, 70.22; H, 7.37; N, 6.82%.

Workup

  1. customit was partitioned between ethyl acetate (200 ml) and 1N HCl (120 ml)
  2. washThe organic layer was washed with more 1N HCl (120 ml), brine (100 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with diethyl ether
  6. filtrationthe white precipitate was collected by filtration
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-0a2a231b4dbf4b118d0c6a5bddcf7782
Source dataset
uspto-grants-2010_04
Patent number
US07705006B2

Reaction notes

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