Water → HCID 21887626, compound

HRID 719822Notes

Reaction equation

HRID 719822 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[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].O>O1CCCC1>[ClH:6].[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]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])[CH2:29][CH2:30][C:24]=2[CH:23]=1)=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 8022Ethyl isocyanateHCID 58737268HCID 58737268, compound

Product 1

HCID 21887626HCID 21887626, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl isocyanate (74 μl) 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 (365 mg) obtained in Example 205 in tetrahydrofuran (2 ml). After stirring at room temperature for 60 minutes, 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 (330 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 (290 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-0135cd644c4c45f995a12afd021cf580
Source dataset
uspto-grants-2006_11
Patent number
US07132547B2

Reaction notes

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