Methylamine → HCID 25030270, compound

HRID 2237515Notes

Reaction equation

HRID 2237515 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][N:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[S:6]1(=[O:23])=[O:22].[CH3:24][NH2:25].C(=O)(O)[O-].[Na+]>CO>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:7]1[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:5]([CH2:4][CH2:3][CH2:2][NH:25][CH3:24])[S:6]1(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 685842831-(3-bromopropyl)-3-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

Product 1

HCID 25030270HCID 25030270, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3-bromopropyl)-3-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.15 g, 0.38 mmol) and an 33% MeNH2 in MeOH (15 mL) was stirred in a sealed tube at room temperature for 16 hours. The reaction was poured into saturated aqueous sodium bicarbonate (20 mL), extracted with ethyl acetate (20 mL), and dried over anhydrous sodium sulfate. The organics were concentrated onto silica gel. Purification via Isco (0-100% dichloromethane containing 15% ammonia in methanol/dichloromethane) followed by treatment with 1 N hydrochloric acid in ether gave 3-[3-(2-fluorophenyl)-2,2-dioxido-3,4-dihydro-1H-2,1,3-benzothiadiazin-1-yl]-N-methylpropan-1-amine (0.056 g, 40%) as an off-white amorphous solid:

Workup

  1. extractionextracted with ethyl acetate (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe organics were concentrated onto silica gel
  4. customPurification via Isco (0-100% dichloromethane containing 15% ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-5ea01f8bd76549468cf777851298606f
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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