Sodium Hydroxide → HCID 24956502, compound

HRID 1095569Notes

Reaction equation

HRID 1095569 reaction equation
FC(F)(F)S(O)(=O)=O.[CH3:9][N:10]([CH3:39])[C:11]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:16][CH2:15][C:14]([C:17]2[NH:18][C:19]3[C:24]([C:25]=2[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH2:12]1.[OH-].[Na+]>C(Cl)Cl>[CH3:39][N:10]([CH3:9])[C:11]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:16][CH2:15][CH:14]([C:17]2[NH:18][C:19]3[C:24]([C:25]=2[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86637921HCID 86637921, compound

Product 1

HCID 24956502HCID 24956502, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-Dimethyl-[1-phenyl-4-(3-pyridin-2-ylmethyl-1H-indol-2-yl)cyclohex-3-enyl]amine Trifluoromethanesulfonic acid (3.95 g, 2.30 ml, 26 mmol) was added to a solution of Ind-49 (2.17 g 10.4 mmol) and Ket-10 (2.70 g, 12.5 mmol) in anhydrous methylene chloride (80 ml), while cooling with ice. The reaction mixture was stirred at room temperature for 2 d and 0.5 M sodium hydroxide solution (50 ml) was then added and the mixture was stirred at room temperature for 2 h. The phases were separated, the aqueous phase was extracted with methylene chloride (3×30 ml) and the combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product (6.45 g) was purified by flash chromatography (400 g, 20×7.6 cm) with chloroform/methanol (9:1).

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture was stirred at room temperature for 2 h
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with methylene chloride (3×30 ml)
  5. dry with materialthe combined organic phases were dried with sodium sulfate
  6. concentrationconcentrated i
  7. customThe crude product (6.45 g) was purified by flash chromatography (400 g, 20×7.6 cm) with chloroform/methanol (9:1)

Sources & evidence

ORD record
ord-3446e2d6886b480998902b89bb698295
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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