Water → HCID 86594133, compound

HRID 2061236Notes

Reaction equation

HRID 2061236 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.Cl.[NH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[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]3CCNCC3)[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[CH2:7][CH2:6][N:3]([C:1]([NH:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:39])[CH2:4][CH2:5]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 2725036Glycine tert-butyl ester hydrochloride

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 t-butyl aminoacetate 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-dbc4992f0cf941de87d611b649e88048
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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