Triethylamine → HCID 23111118, compound

HRID 1920503Notes

Reaction equation

HRID 1920503 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(N=C=N[CH2:23][CH2:24][CH2:25]N(C)C)C.C([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(C)(C)C.[CH2:40](N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:24]([C:37]1[CH:36]=[CH:35][C:34]([NH:33][C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:16])=[CH:39][CH:38]=1)([CH3:25])([CH3:40])[CH3:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 254260N-(1,1-Dimethylethyl)benzenamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 23111118HCID 23111118, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Piperidine-1,4-dicarboxylic acid mono-t-butyl ester (10.6 g) was dissolved in dichloromethane (100 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.8 g), t-butylaniline (7.3 ml), and triethylamine (12.9 ml) were added, and the mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. The solvent was evaporated, a 4N solution (140 ml) of hydrogen chloride in dioxane and dioxane (60 ml) were added to the obtained residue, and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated to give the title compound as a crude product.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. additiona 4N solution (140 ml) of hydrogen chloride in dioxane and dioxane (60 ml) were added to the obtained residue
  5. stirringthe mixture was stirred at room temperature for 2 hours
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-949d7a183e1846f38365a08336dc963a
Source dataset
uspto-grants-2012_05
Patent number
US08168827B2

Reaction notes

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