Dichloromethane → (2S)-N-[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl]-N,4-dimethyl-2-(methylamino)pentanamide hydrochloride

HRID 2236005Notes

Reaction equation

HRID 2236005 reaction equation
FC(F)(F)C(O)=O.[CH:8]1[C:18]2[CH:17]=[CH:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[C:13](=[CH:23][CH2:24][CH2:25][N:26]([CH3:43])[C:27]([C@@H:29]([N:34](C)[C:35](=O)OC(C)(C)C)[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:28])[C:12]=2[CH:11]=[CH:10][CH:9]=1.[Cl:44]CCl>>[ClH:44].[CH:19]1[C:15]2[CH:16]=[CH:17][C:18]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13](=[CH:23][CH2:24][CH2:25][N:26]([CH3:43])[C:27](=[O:28])[C@@H:29]([NH:34][CH3:35])[CH2:30][CH:31]([CH3:33])[CH3:32])[C:14]=2[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59853865t-butyl (1S)-1-{[[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl] (methyl) amino]carbonyl}-3-methylbutyl(methyl)carbamate

Product 1

HCID 68420933(2S)-N-[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl]-N,4-dimethyl-2-(methylamino)pentanamide hydrochloride

Procedure

5 ml of dichloromethane and 2.5 ml of trifluoroacetic acid were added to 169 mg (0.35 mmol) of t-butyl (1S)-1-{[[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl] (methyl) amino]carbonyl}-3-methylbutyl(methyl)carbamate, and they were stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. 1 N aqueous sodium hydroxide solution was added thereto to make it basic. After extracting with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was dissolved in 5 ml of 1,4-dioxane. 4 N hydrochloric acid/1,4-dioxane solution was added to the obtained solution. The resultant mixture was concentrated under reduced pressure to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. addition1 N aqueous sodium hydroxide solution was added
  3. extractionAfter extracting with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 5 ml of 1,4-dioxane
  7. addition4 N hydrochloric acid/1,4-dioxane solution was added to the obtained solution
  8. concentrationThe resultant mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-14e8fccb0be946c58a4daf2e44ce9555
Source dataset
uspto-grants-2010_05
Patent number
US07713957B2

Reaction notes

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