1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(Phenylmethyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

HRID 1627459Notes

Reaction equation

HRID 1627459 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[C:13]1([CH2:19][C:20]([NH:22][C:23]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[C:13]1([CH2:19][C:20]2[O:31][C:29](=[O:30])[C:23]3([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[N:22]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18417075HCID 18417075, compound

Product 1

HCID 247398022-(Phenylmethyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-oneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

633 mg (3.3 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 784 mg (3 mmol) of 1-[(phenylacetyl)amino]cyclohexanecarboxylic acid obtained in Reference Example 2 in 20 ml of methylene chloride. After the mixture was stirred at room temperature for 4 hours, the reaction solution was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 625 mg (86%) of the title compound.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was successively washed with water
  4. dry with materialby drying with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-44c24b5a49ed4b32b825c85d012e6fc2
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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