Potassium Iodide → N-Methyl-3-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)propan-1-amine

HRID 1917202Notes

Reaction equation

HRID 1917202 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]1=2.Cl.[CH3:19][NH2:20].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:19][NH:20][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]1=2

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 6364545Methylamine hydrochlorideHCID 591440694-(3-Chloropropyl)-7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

Product 1

HCID 59144086N-Methyl-3-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)propan-1-amineYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(3-chloropropyl)-7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine (1.1 g, 4.03 mmol), methylamine hydrochloride (0.545 g, 8.07 mmol), potassium iodide (0.669 g, 4.03 mmol), and potassium carbonate (2.79 g, 20.16 mmol) in dry acetonitrile (25 mL) was stirred at 80° C. in a sealed tube for 6 hours. The reaction was brought to room temperature and diluted with water (100 mL), and the product was extracted into ethyl acetate (3×25 mL). The combined ethyl acetate layers were washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated, and the crude material was purified by flash column chromatography (1:9 (2M NH3 in MeOH):CH2Cl2) on silica gel to obtain the title compound (0.8 g, 74%) as a thick syrup. 1H NMR (DMSO-d6) δ 7.84-7.81 (m, 2H), 6.86 (d, 1H, J=9.9 Hz), 3.78-3.75 (m, 2H), 3.50 (t, 2H, J=7.5 Hz), 3.08-3.04 (m, 2H), 2.48 (t, 2H, J=6.9 Hz), 2.27 (s, 3H), 1.74-1.64 (m, 2H); ESI-MS (m/z, %): 268 (MH+, 100).

Workup

  1. customwas brought to room temperature
  2. extractionthe product was extracted into ethyl acetate (3×25 mL)
  3. washThe combined ethyl acetate layers were washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe crude material was purified by flash column chromatography (1:9 (2M NH3 in MeOH):CH2Cl2) on silica gel

Sources & evidence

ORD record
ord-0a75ef6586764c5492dff6d8adae1e34
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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