Triethylamine → HCID 69299670, compound

HRID 131264Notes

Reaction equation

HRID 131264 reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[CH3:14][N:15]([CH3:20])[CH2:16][CH2:17][CH2:18][OH:19].[CH3:21][N:22]([CH3:37])[CH2:23][CH2:24][NH:25][CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:37][N:22]([CH3:21])[CH2:23][CH2:24][N:25]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:35][CH:36]=1)[C:2]([O:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:20])[CH3:14])=[O:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 766463-(Dimethylamino)-1-propanolHCID 821294-Nitrophenyl chloroformateHCID 16781125HCID 16781125, compound

Product 1

HCID 69299670HCID 69299670, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of p-nitrophenyl chloroformate (18.1 g) in methylene chloride (300 mL) is added dropwise 3-(dimethylamino)propanol (14.2 mL) and the mixture is stirred at room temperature for 4 hours. To the mixture is added successively methyl 4-[[[2-(dimethylamino)ethyl]amino]methyl]benzoate (13.7 g) and triethylamine (25 mL) and the mixture is stirred at room temperature for one day. The reaction mixture is washed with a saturated potassium carbonate solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The resultant crude product is purified by flash column chromatography on NH-silica gel (Chromatorex NH silica gel, Solvent; ethyl acetate:n-hexane=1:1) to give methyl 4-[[N-[2-(dimethylamino)ethyl]-N-[[3-(dimethylamino)propoxy]carbonyl]amino]methyl]benzoate (7.97 g, yield; 38%) as a colorless oil. MS (APCI) m/z: 366 [M+H]+

Workup

  1. stirringthe mixture is stirred at room temperature for one day
  2. washThe reaction mixture is washed with a saturated potassium carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant crude product is purified by flash column chromatography on NH-silica gel (Chromatorex NH silica gel, Solvent; ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-5561329a021746309e6b6419c852cef8
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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