Water → HCID 86594133, compound

HRID 2236016Notes

Reaction equation

HRID 2236016 reaction equation
[CH2:1](N(CC)CC)C.[C:8](Cl)([CH3:11])([CH3:10])[CH3:9].[NH2:13][CH2:14][C:15]([OH:17])=[O:16].[CH:18]1[C:28]2[CH:27]=[CH:26][C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[C:23](=[C:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[C:22]=2[CH:21]=[CH:20][CH:19]=1.[OH2:39]>O1CCCC1>[CH:18]1[C:28]2[CH:27]=[CH:26][C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[C:23](=[C:33]3[CH2:34][CH2:35][N:36]([C:1]([NH:13][CH2:14][C:15]([O:17][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:16])=[O:39])[CH2:37][CH2:38]3)[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidineHCID 86595916HCID 86595916, compound

Product 1

HCID 86594133HCID 86594133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

475 mg (2.93 mmol) of N,N′-carbonyldiimidazole was dissolved in 10 ml of anhydrous tetrahydrofuran. 0.45 ml (3.29 mmol) of triethylamine was added to the obtained solution, and they were stirred at room temperature for 10 minutes. The reaction mixture was cooled with ice, and 460 mg (2.74 mmol) of glycine t-butyl hydrochloride was added dropwise to the mixture during a period of about 10 minutes, and they were stirred at room temperature for 1 hour. After cooling with ice, 500 mg (1.83 mmol) of 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)piperidine was added to the resultant mixture, and they were stirred at room temperature overnight. Water was added to the reaction mixture. After extracting with ethyl acetate followed by drying over anhydrous magnesium sulfate, the product was concentrated under reduced pressure. The residue thus obtained was purified by the silica gel chromatography (dichloromethane: methanol=95:5 to 2:3) to obtain the title compound.

Workup

  1. additionwas added dropwise to the mixture during a period of about 10 minutes
  2. stirringthey were stirred at room temperature for 1 hour
  3. stirringwere stirred at room temperature overnight
  4. extractionAfter extracting with ethyl acetate
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. concentrationthe product was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by the silica gel chromatography (dichloromethane: methanol=95:5 to 2:3)

Sources & evidence

ORD record
ord-4fe5f546bb1642ab883507649540bb1e
Source dataset
uspto-grants-2010_05
Patent number
US07713957B2

Reaction notes

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