Sodium Iodide → HCID 14181068, compound

HRID 487942Notes

Reaction equation

HRID 487942 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[S:7]1(=[O:17])=[O:16].[CH3:18][O:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[CH2:28][CH:27]([NH:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:25]2.[I-].[Na+].NC1C2C(=CC=CC=2)CCC1>CN(C)C=O.C(N(CC)CC)C>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[CH2:28][CH:27]([N:30]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[S:7]1(=[O:17])=[O:16])[CH2:31][CH2:32][CH3:33])[CH2:26][CH2:25]2

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 107817741,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-oneHCID 127414178-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 14181068HCID 14181068, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent2×

Procedure

1.9 g (6.0 mmol) of 2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide were added dropwise to the solution of the 1.3 g (6.0 mmol) of 8-methoxy-2-propylamino-1,2,3,4-tetrahydronaphthalene and 1.3 g (12 mmol) of triethylamine in 15 ml of dimethylformamide. After stirring for 15 hours at room temperature, a spatula tip of sodium iodide was added, and the mixture was heated to 60° C. After 4 hours at this temperature, 0.4 g of the above aminotetralin and 0.3 g of triethylamine were added. Chromatography on silica gel (toluene/ethyl acetate gradients) of the crude product, obtained after removal of the solvent in vacuo, yielded 0.70 g (25%) of the title compound as a yellowish oil.

Workup

  1. temperaturethe mixture was heated to 60° C
  2. customChromatography on silica gel (toluene/ethyl acetate gradients) of the crude product, obtained
  3. customafter removal of the solvent in vacuo

Sources & evidence

ORD record
ord-f329a30f2b1c4493866c514ae81c9916
Source dataset
uspto-grants-1994_03
Patent number
US05298513

Reaction notes

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