Sodium Hydroxide → AM-1248

HRID 1161611Notes

Reaction equation

HRID 1161611 reaction equation
[Cl-].C([Al+]CC)C.[C:7]12([C:17](Cl)=[O:18])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][N:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29]1.[OH-].[Na+]>CCCCCC.C(Cl)Cl>[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][N:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([C:17]([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]4)[CH2:8]2)[CH2:14]3)=[O:18])=[CH:29]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 989151-Adamantanecarbonyl chlorideHCID 11550392N-(N-Methylpiperidinyl)methylindoleHCID 16686102Diethyl aluminum chloride

Product 1

HCID 10293794AM-1248

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8058HexaneSolvent

Procedure

To the stirring solution of the diethyl aluminum chloride (1.5 ml 1 M soln. in hexane, 180.8 mg, 1.5 mmol) in 10 ml absolute methylene chloride was added at room temp. 298.0 mg (1.5 mmol) 1-adamantanecarbonyl chloride in 5 ml of methylene chloride and the reaction mixture was stirred 15 min. The solution of (N-Methyl-2-piperidinyl)methyl-1H-indole (228.3 mg, 1.0 mmol) in 5 ml of methylene chloride was added during 3 min and mixture was stirred and reflux 48 h. The reaction was work-up by addition of 20 ml 2M solution of sodium hydroxide and extracted by ethyl acetate (3×20 ml), washed to times by water and two times by brine. The combined extract dried by the mixture of sodium sulfate and potassium carbonate. After removing of solvents the rest was purified by chromatography (silica gel, methanol ethyl acetate 1:1).

Workup

  1. temperaturereflux 48 h
  2. extractionextracted by ethyl acetate (3×20 ml)
  3. washwashed to times by water and two times by brine
  4. extractionThe combined extract
  5. dry with materialdried by the mixture of sodium sulfate and potassium carbonate
  6. customAfter removing of solvents the rest
  7. customwas purified by chromatography (silica gel, methanol ethyl acetate 1:1)

Sources & evidence

ORD record
ord-e10fd40b3a9b4589a2d82b924b0257e3
Source dataset
uspto-grants-2010_10
Patent number
US07820144B2

Reaction notes

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