n-[2-(Ethylamino)ethyl]phthalimide hydrochloride salt → N-[2-(ethylamino)ethyl]phthalimide

HRID 2273613Notes

Reaction equation

HRID 2273613 reaction equation
Cl.[CH2:2]([NH:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17])[CH3:3]>ClCCl>[CH2:2]([NH:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17])[CH3:3]

Participants

3

Reactant 1

HCID 66944064n-[2-(Ethylamino)ethyl]phthalimide hydrochloride salt

Product 1

HCID 21748445N-[2-(ethylamino)ethyl]phthalimideYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of N-[2-(ethylamino)ethyl]phthalimide hydrochloride salt (1) (2.00 g, 7.86 mmol) (Jones, J. H.; Holtz, W. J.; Cragoe, E. J. 6-Substituted 5-chloro-1,3-dihydro-2H-imidazo[4,5-b]pyrazin-2-ones with hypotensive activity. J. Med. Chem. 1973, 16, 537-42) in dichloromethane (100 mL) was washed with a 5% aqueous sodium carbonate solution (5 mL). The mixture was extracted with dichloromethane (40 mL). The organic layers were combined, dried on magnesium sulfate, filtered and evaporated under vacuum to give compound 2 (1.41 g, 6.47 mmol) as a yellow solid. Yield 82%; mp 111-113° C. (dec.); IR (KBr) ν 1292, 1395, 1430, 1541, 1637, 1712, 2929, 3200-3600 cm−; 1H NMR (200 MHz, CDCl3) δ 1.07 (t, 3H, J=7.1 Hz), 2.68 (q, 2H, J=7.1 Hz), 2.92 (t, 2H, J=6.5 Hz), 3.81 (t, 2H, J=6.5 Hz), 7.68 (m, 2H), 7.82 (m, 2H).

Workup

  1. washwas washed with a 5% aqueous sodium carbonate solution (5 mL)
  2. extractionThe mixture was extracted with dichloromethane (40 mL)
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-ba18e9ec766f40c8a836881a6ff5a542
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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