Hydrochloric Acid → 2-Methyl-1-{7-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethoxy]-1H-indol-3-yl}propan-2-amine

HRID 1351985Notes

Reaction equation

HRID 1351985 reaction equation
[CH3:1][C:2]([NH:25]C(=O)OC(C)(C)C)([CH3:24])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][C@@H:14]([CH3:23])[C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.Cl.C(=O)([O-])O.[Na+]>C(Cl)Cl.O1CCOCC1>[CH3:1][C:2]([NH2:25])([CH3:24])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][C@@H:14]([CH3:23])[C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86604034tert-butyl (1,1-dimethyl-2-{7-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethoxy]-1H-indol-3-yl}ethyl)carbamate

Product 1

HCID 694581352-Methyl-1-{7-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethoxy]-1H-indol-3-yl}propan-2-amineYield 53.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (1,1-dimethyl-2-{7-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethoxy]-1H-indol-3-yl}ethyl)carbamate (166 mg, 0.373 mmol) in methylene chloride (2 mL) is added a 4N hydrogen chloride solution in dioxane (0.5 mL), and the mixture is stirred at room temperature for 3 hours. The reaction solution is poured into a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is dried over anhydrous magnesium sulfate, and the solvent is evaporated. The obtained crude product is purified by silica gel column chromatography (a saturated ammonia solution in chloroform ) a saturated ammonia solution in chloroform-methanol=50:1) to give the title compound (68.4 mg, yield: 53%).

Workup

  1. extractionthe mixture is extracted with chloroform
  2. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  3. customthe solvent is evaporated
  4. customThe obtained crude product
  5. customis purified by silica gel column chromatography (a saturated ammonia solution in chloroform ) a saturated ammonia solution in chloroform-methanol=50:1)

Sources & evidence

ORD record
ord-dd418bb49995460480958d08c9df89a4
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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