1,3-Benzodioxole-5-carboxylic acid → ethyl 1-[N-(3,4-methylenedioxyphenylcarbonyl) amino]cyclohexanecarboxylate

HRID 1953426Notes

Reaction equation

HRID 1953426 reaction equation
[CH2:1]1[O:12][C:11]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=2[O:2]1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[NH2:47][C:48]1([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1>ClCCl>[CH2:1]1[O:12][C:11]2[CH:10]=[CH:9][C:5]([C:6]([NH:47][C:48]3([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]3)=[O:8])=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 5

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11241228Ethyl 1-aminocyclohexane-1-carboxylate hydrochloride

Product 1

HCID 23297898ethyl 1-[N-(3,4-methylenedioxyphenylcarbonyl) amino]cyclohexanecarboxylateYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.74 g (16.5 mmol) of 3,4-methylenedioxybenzoic acid was dissolved in anhydrous dichloromethane and then was ice cooled. 4.62 ml (33.0 mmol) of triethylamine, 2.53 g (16.5 mmol) of 1-hydroxybenzotriazole hydrate, 3.57 g (17.3 mmol) of N,N'-dicyclohexylcarbodiimide and 3.20 g (16.5 mmol) of ethyl 1-aminocyclohexanecarboxylate hydrochloride were successively added to the above reaction mixture and were stirred for 18 hours gradually rising the temperature up to the room temperature. The reaction mixture was concentrated under reduced pressure and was dissolved in ethyleacetate, and the insoluble components were removed therefrom by filtration. After the ethyl acetate solution was washed successively with 1N-hydrochloric acid, saturated brine, aqueous solution of saturated sodium hydrogen carbonate and saturated brine, the resultant organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, whereby 5.21 g of ethyl 1-[N-(3,4-methylenedioxyphenylcarbonyl)amino]cyclohexanecarboxylate was obtained.

Workup

  1. temperaturecooled
  2. customup to the room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionwas dissolved in ethyleacetate
  5. customthe insoluble components were removed
  6. filtrationby filtration
  7. washAfter the ethyl acetate solution was washed successively with 1N-hydrochloric acid, saturated brine, aqueous solution of saturated sodium hydrogen carbonate and saturated brine
  8. dry with materialthe resultant organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4198493af5448c2aa55bb25495796f5
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

Loading…