Triethylamine → HCID 59853925, compound

HRID 2061226Notes

Reaction equation

HRID 2061226 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[CH3:13][NH:14][CH2:15][CH2:16][CH:17]=[C:18]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH2:26][CH2:25][C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]1=2.Cl.C(N(CC)CC)C.[C:41]([O:45][C:46]([NH:48][CH2:49][C:50]([OH:52])=O)=[O:47])([CH3:44])([CH3:43])[CH3:42].C(=O)([O-])O.[Na+]>ClCCl>[CH:23]1[C:24]2[CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:18](=[CH:17][CH2:16][CH2:15][N:14]([CH3:13])[C:50](=[O:52])[CH2:49][NH:48][C:46](=[O:47])[O:45][C:41]([CH3:42])([CH3:43])[CH3:44])[C:19]=2[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 441358Nortriptyline hydrochlorideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59853925HCID 59853925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

281 mg (1.47 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride, 281 mg (1.47 mmol) of nortriptyline hydrochloride and 0.40 ml (2.87 mmol) of triethylamine were added to 251 mg (1.44 mmol) of t-butoxycarbonylglycine in 10 ml of dichloromethane, and they were stirred at room temperature overnight. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture. After extracting with dichloromethane, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate=4:1) to obtain the title compound.

Workup

  1. extractionAfter extracting with dichloromethane
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-15ad7f9a10b541bba7956b5d9bc00c28
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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