Triethylamine → HCID 53919312, compound

HRID 1417475Notes

Reaction equation

HRID 1417475 reaction equation
C(N(CC)CC)C.Br[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[C:20]1([CH:26]2[C:38]3[NH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:30]=3[CH2:29][CH2:28][NH:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C.CCCCCC.O>[C:20]1([CH:26]2[C:38]3[NH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:30]=3[CH2:29][CH2:28][N:27]2[CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

9

Reactant 4

HCID 8471Triethylamine2×HCID 62576Benzyl bromoacetate2×HCID 1989671-Phenyl-2,3,4,9-tetrahydro-1H-beta-carbolineHCID 516892Sodium Bicarbonate

Product 1

HCID 53919312HCID 53919312, compoundYield 102.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

147 mg (1.45 mmol) of triethylamine and 277 mg (1.21 mmol) of benzyl bromoacetate were added successively to a solution of 300 mg (1.21 mmol) of 1-phenyl-1,2,3,4-tetrahydro-β-carboline, as obtained in Example 70, in 10 ml of methylene chloride, with ice-cooling, and the resulting mixture was stirred at room temperature for 3 hours. After this time, 277 mg of benzyl bromoacetate and 183 mg of triethylamine were added to the reaction mixture, and the resulting mixture was allowed to stand for 2 days. At the end of this time, first a saturated aqueous solution of sodium hydrogencarbonate and then water were added successively to the reaction mixture, which was then extracted with ethyl acetate. The resulting extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and the ethyl acetate was removed by evaporation under reduced pressure to give 0.61 g of a crude mixture. The resulting residue was subjected to column chromatography using 13 g of silica gel with a 9:1 by volume mixture of hexane and ethyl acetate as the eluent, to yield 0.49 g of the title compound as yellow crystals in quantitative yield. The product was subsequently recrystallized from ethyl acetate to yield 0.37 g of the title compound as yellow crystals, melting at 130.8°-132.0° C.

Workup

  1. temperaturecooling
  2. waitto stand for 2 days
  3. extractionwas then extracted with ethyl acetate
  4. extractionThe resulting extract
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe ethyl acetate was removed by evaporation under reduced pressure
  8. customto give 0.61 g of a crude mixture

Sources & evidence

ORD record
ord-6e75f1f8d94943dbaed3044efffdb4a0
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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