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

HRID 1917199Notes

Reaction equation

HRID 1917199 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.[CH3:18][NH:19][CH3:20].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:18][N:19]([CH3:20])[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 674DimethylamineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 591440694-(3-Chloropropyl)-7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

Product 1

HCID 59144154N,N-Dimethyl-3-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)propan-1-amineYield 42%

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 (0.7 g, 2.57 mmol), dimethylamine (2M solution in THF) (2.57 mL, 5.13 mmol), potassium iodide (0.426 g, 2.57 mmol), and potassium carbonate (1.773 g, 12.83 mmol) in dry acetonitrile (20 mL) was stirred at 80° C. for 6 hours in a sealed tube. The reaction was then brought to room temperature and diluted with water (60 mL), and the product was extracted into ethyl acetate (3×20 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 column chromatography (1:9 (2 M NH3 in MeOH):CH2Cl2) on silica gel to obtain the title product (0.3 g, 42%) as a thick syrup. 1H NMR (DMSO-d6) δ 7.85-7.80 (m, 2H), 6.85 (d, 1H, J=8.7 Hz), 3.77 (t, 2H, J=5.1 Hz), 3.47 (t, 2H, J=7.2 Hz), 3.06 (t, 2H, J=5.1 Hz), 2.24 (t, 2H, J=6.6 Hz), 2.14 (s, 6H), 1.75-1.65 (m, 2H); ESI-MS (m/z, %): 282 (MH+, 100).

Workup

  1. customwas then brought to room temperature
  2. extractionthe product was extracted into ethyl acetate (3×20 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 column chromatography (1:9 (2 M NH3 in MeOH):CH2Cl2) on silica gel

Sources & evidence

ORD record
ord-38c1b15f58ce49cd9073bd59d8f01e61
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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