Water → HCID 21888122, compound

HRID 719821Notes

Reaction equation

HRID 719821 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][N:15]([CH3:33])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([C:22]1[CH:32]=[CH:31][C:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH2:30][C:24]=2[CH:23]=1)=[O:21].C(N(CC)CC)C.O>O1CCCC1>[ClH:5].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][N:15]([CH3:33])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([C:22]1[CH:32]=[CH:31][C:25]2[CH2:26][CH2:27][N:28]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:29][CH2:30][C:24]=2[CH:23]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58737268HCID 58737268, compound

Product 1

HCID 21888122HCID 21888122, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylsulfonyl chloride (4511) was added to a solution of 5-[[2-(2-chlorophenyl)ethyl](methyl)amino]-1-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1-pentanone (223 mg) obtained in Example 205 and triethylamine (13911) in tetrahydrofuran (2 ml). After stirring at room temperature for 60 minute, water (10 g) was added, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give a free base compound of the title compound as a pale yellow oil (230 mg). A solution of the free base compound in ethanol was treated with hydrogen chloride (ethyl acetate solution) to give the title compound as pale yellow amorphous powders (200 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1bbf8df0c3354285b8a3dbc0f6356b21
Source dataset
uspto-grants-2006_11
Patent number
US07132547B2

Reaction notes

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