Sodium Carbonate → 8-Methoxy-N-propyl-N-[3-(2,3-dihydro-1,1-dioxo-3-oxo-1,2-benzisothiazolyl)propyl]-2-aminotetralin

HRID 2270506Notes

Reaction equation

HRID 2270506 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:8]2.I[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=2[S:22]1(=[O:32])=[O:31].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:13]([CH2:14][CH2:15][CH3:16])[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=3[S:22]1(=[O:32])=[O:31])[CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 127414178-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amineHCID 18331848N-(3-iodopropyl)-2,3-dihydro-1,1-dioxo-3-benzisothiazolone

Product 1

HCID 183318118-Methoxy-N-propyl-N-[3-(2,3-dihydro-1,1-dioxo-3-oxo-1,2-benzisothiazolyl)propyl]-2-aminotetralin

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8-Methoxy-N-propyl-2-aminotetralin (Arvidsson L.-E. et al., J. Med. Chem., 27, 45 (1984) (2 g, 10 mmol), N-(3-iodopropyl)-2,3-dihydro-1,1-dioxo-3-benzisothiazolone (7.5 g), sodium carbonate (2.5 g), and acetonitrile (25 ml) were heated to reflux for 24 hours. After cooling, the solvent was removed in vacuo and the residue placed on a flash silica gel column (3 cm×35 cm) and eluted with ethyl acetate/hexane (5:95, 10:90, 15:85, 20:80, successively). Solvent removal in vacuo afforded the title compound as a white powder (m.p. 131° C.).

Workup

  1. temperatureto reflux for 24 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. washeluted with ethyl acetate/hexane (5:95, 10:90, 15:85, 20:80
  5. customSolvent removal in vacuo

Sources & evidence

ORD record
ord-3a20203ef56a4eaa9097ac9737214179
Source dataset
uspto-grants-2001_12
Patent number
US06331636B1

Reaction notes

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