Triethylamine → HCID 67234880, compound

HRID 1913273Notes

Reaction equation

HRID 1913273 reaction equation
Cl.N1CCC1.Cl.CN(C)CCCN=C=NCC.[OH:18]N1C2C=CC=CC=2N=N1.[CH2:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])C.[CH2:35]([O:42][C:43]1([CH:51]=[CH:50]C=[CH:48][CH2:47]1)C([O-])=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O.CN(C)C=O>[CH2:35]([O:42][C:43]1[CH:47]=[CH:48][C:34]([C:33]([N:30]2[CH2:28][CH2:32][CH2:31]2)=[O:18])=[CH:50][CH:51]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12308726Azetidine hydrochlorideHCID 86654430HCID 86654430, compound

Product 1

HCID 67234880HCID 67234880, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Azetidine hydrochloride (10.3 g, 110 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (25.2 g, 131 mmol), 1-hydroxybenzotriazole (20.1 g, 131 mmol), and triethylamine (33.6 ml, 241 mmol) were added to a N,N-dimethylformamide solution (500 ml) of 1-(benzyloxy)benzoate (25 g, 110 mmol), and this mixture was stirred overnight at room temperature. Water was added to this reaction solution, this mixture was extracted with ethyl acetate twice, followed by washing the organic layer with water and a saturated saline solution, drying the organic layer with anhydrous sodium sulfate, and thereafter concentrating this solvent under reduced pressure. The obtained residue was crystallized from chloroform-diethyl ether to obtain 1-[4-(benzyloxy)-benzoyl]azetidine (23.0 g, yield: 79%) as an ecru solid.

Workup

  1. extractionthis mixture was extracted with ethyl acetate twice
  2. washby washing the organic layer with water
  3. dry with materiala saturated saline solution, drying the organic layer with anhydrous sodium sulfate
  4. concentrationconcentrating this solvent under reduced pressure
  5. customThe obtained residue was crystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-f430c36cde244a4aaf4f83928cf7962c
Source dataset
uspto-grants-2013_12
Patent number
US08609699B2

Reaction notes

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