Triethylamine → N-[2-[4-(5H-dibenzo[a,d] [7]annulen-5-ylidene)-1-piperidinyl]-1-(hydroxymethyl)-2-oxoethyl]-1-piperidinecarboxamide

HRID 2061240Notes

Reaction equation

HRID 2061240 reaction equation
[OH:1][CH2:2][CH:3]([NH:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9])[C:4]([OH:6])=O.[CH:16]1[C:26]2[CH:25]=[CH:24][C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[C:21](=[C:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>ClCCl>[CH:16]1[C:26]2[CH:25]=[CH:24][C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[C:21](=[C:31]3[CH2:32][CH2:33][N:34]([C:4](=[O:6])[CH:3]([NH:7][C:8]([N:10]4[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]4)=[O:9])[CH2:2][OH:1])[CH2:35][CH2:36]3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 611830273-Hydroxy-2-[(1-piperidinylcarbonyl)amino]propionic acid

Product 1

HCID 59853888N-[2-[4-(5H-dibenzo[a,d] [7]annulen-5-ylidene)-1-piperidinyl]-1-(hydroxymethyl)-2-oxoethyl]-1-piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

64.0 mg (0.296 mmol) of 3-hydroxy-2-[(1-piperidinylcarbonyl)amino]propionic acid, 80.9 mg (0.296 mmol) of 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)piperidine and 85.1 mg (0.444 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride were dissolved in 10 ml of dichloromethane. 0.091 ml (0.651 mmol) of triethylamine was added to the obtained solution, and they were stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue. After washing with saturated aqueous sodium chloride solution, the reaction product was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resultant product was purified by the silica gel chromatography (dichloromethane:methanol=9:1) to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washAfter washing with saturated aqueous sodium chloride solution
  4. dry with materialthe reaction product was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant product was purified by the silica gel chromatography (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-2a63881cd50847c58910c3b0db02efd6
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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