Methylamine → 3-(2,2-dioxido-1-phenyl-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)-N-methylpropan-1-amine hydrochloride

HRID 2237468Notes

Reaction equation

HRID 2237468 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[S:6]1(=[O:22])=[O:21].[CH3:23][NH2:24]>O1CCCC1>[ClH:1].[O:21]=[S:6]1(=[O:22])[N:5]([CH2:4][CH2:3][CH2:2][NH:24][CH3:23])[CH2:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 685821793-(3-chloropropyl)-1-phenyl-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

Product 1

HCID 685819143-(2,2-dioxido-1-phenyl-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)-N-methylpropan-1-amine hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

3-(3-chloropropyl)-1-phenyl-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.030 g, 0.089 mmol) was dissolved in an 8 M solution of methylamine in tetrahydrofuran (5 mL), treated with KI (0.030 g, 0.18 mmol), and stirred in a capped vial at 50° C. for 20 hours. The reaction mixture was evaporated and the residue purified by flash chromatography (SiO2, 0-5% 7 M NH3-methanol/dichloromethane). The purified free-base was dissolved in ethyl ether (10 mL) and treated with hydrogen chloride (1.0 mL of a 2 M solution in ethyl ether), resulting in a white precipitate that was isolated by decantation and dried under vacuum to afford 3-(2,2-dioxido-1-phenyl-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)-N-methylpropan-1-amine hydrochloride (0.030 g, 92%) as a white solid:

Workup

  1. additiontreated with KI (0.030 g, 0.18 mmol)
  2. customThe reaction mixture was evaporated
  3. customthe residue purified by flash chromatography (SiO2, 0-5% 7 M NH3-methanol/dichloromethane)
  4. dissolutionThe purified free-base was dissolved in ethyl ether (10 mL)
  5. additiontreated with hydrogen chloride (1.0 mL of a 2 M solution in ethyl ether),
  6. customresulting in a white precipitate that
  7. customwas isolated by decantation
  8. customdried under vacuum

Sources & evidence

ORD record
ord-7781354858e045018c68df4b0b9116c5
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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