Ethyl chloroformate → Benzamide, 4-(acetylamino)-5-chloro-N-[(2-ethyloctahydrocyclopenta[c]pyrrol-1-yl)methyl]-2-methoxy-

HRID 1833407Notes

Reaction equation

HRID 1833407 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[C:9]([Cl:16])=[CH:8][C:4]=1[C:5]([OH:7])=O.ClC(OCC)=O.[CH2:23]([N:25]1[CH2:32][CH:31]2[CH:27]([CH2:28][CH2:29][CH2:30]2)[CH:26]1[CH2:33][NH2:34])[CH3:24]>O1CCCC1.C(N(CC)CC)C>[CH2:23]([N:25]1[CH2:32][CH:31]2[CH:27]([CH2:28][CH2:29][CH2:30]2)[CH:26]1[CH2:33][NH:34][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([Cl:16])[C:10]([NH:12][C:13](=[O:15])[CH3:14])=[CH:11][C:3]=1[O:2][CH3:1])[CH3:24]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acidHCID 85848305HCID 85848305, compound

Product 1

HCID 86733791Benzamide, 4-(acetylamino)-5-chloro-N-[(2-ethyloctahydrocyclopenta[c]pyrrol-1-yl)methyl]-2-methoxy-

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 6 parts of 2-methoxy-4-acetylamino-5-chloro benzoic acid in 50 parts of anhydrous tetrahydrofuran, were added 2.5 parts of triethylamine. The solution thus obtained was poured portionwise in a mixture of 2.7 parts of ethyl chloroformate in 80 parts of tetrahydrofuran maintained at 0° C. After stirring for 10 minutes, 4.1. parts of N-ethyl-2-aminomethyl-3-azabicyclo (3,3,0) octane were added. After being maintained at room temperature for 10 minutes, the temperature was progressively increased and, finally, the reaction mixture was refluxed for 60 minutes. After cooling, the mixture was filtered and the filtrate was evaporated in vacuo. After recrystallization in 50 parts of ethyl acetate, there were obtained 5.5 parts of N-ethyl-2-(2-methoxy-4-acetylamino-5-chloro benzamido methyl)-3-azabicyclo (3,3,0) octane, M.P. 156°-157° C (ethyl acetate).

Workup

  1. customThe solution thus obtained
  2. temperatureAfter being maintained at room temperature for 10 minutes
  3. temperaturethe temperature was progressively increased
  4. temperaturefinally, the reaction mixture was refluxed for 60 minutes
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered
  7. customthe filtrate was evaporated in vacuo
  8. customAfter recrystallization in 50 parts of ethyl acetate

Sources & evidence

ORD record
ord-cfafa8d9228a466abce7c71a51184e64
Source dataset
uspto-grants-1978_01
Patent number
US04066662

Reaction notes

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