Triethylamine → HCID 59853915, compound

HRID 2061206Notes

Reaction equation

HRID 2061206 reaction equation
Cl.[CH:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[C:17]3[CH2:22][CH2:21][N:20](C(N)C=O)[CH2:19][CH2:18]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:27]([N:29](CC)CC)[CH3:28].Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36].C(=O)([O-])[OH:41].[Na+]>ClCCl>[CH:13]1[C:9]2[CH:10]=[CH:11][C:12]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=3[C:7](=[C:17]3[CH2:22][CH2:21][N:20]([C:28](=[O:41])[CH2:27][NH:29][C:35](=[O:36])[O:37][CH2:38][CH3:39])[CH2:19][CH2:18]3)[C:8]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 86594131HCID 86594131, compound

Product 1

HCID 59853915HCID 59853915, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

375 mg (1.00 mmol) of 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl-2-oxoethanamine hydrochloride was dissolved in 3 ml of dichloromethane. 303 mg (3.00 mmol) of triethylamine was added to the obtained solution. Then a solution of 130 mg (1.20 mmol) of ethyl chloroformate in 3 ml of dichloromethane was slowly added to the reaction mixture. After stirring overnight, saturated aqueous sodium hydrogencarbonate solution was added thereto. After extracting with ethyl acetate twice followed by drying under anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was roughly purified by the silica gel chromatography (dichloromethane:methanol=98:2) and then purified by the silica gel chromatography (hexane:ethyl acetate=1:2) to obtain the title compound.

Workup

  1. extractionAfter extracting with ethyl acetate
  2. customby drying under anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was roughly purified by the silica gel chromatography (dichloromethane:methanol=98:2)
  5. custompurified by the silica gel chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-687522a13db244d499ee84ffae86d054
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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