Ammonia → HCID 86754401, compound

HRID 1585229Notes

Reaction equation

HRID 1585229 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([CH:12]1[CH:20]2[C:15]([C:31]([OH:33])=O)([CH2:16][C:17]3[CH:30]=[CH:29][CH:28]=[CH:27][C:18]=3[CH:19]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14][NH:13]1)=[O:11].[NH3:34]>ClCCl.C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([CH:12]1[CH:20]2[C:15]([C:31]([NH2:34])=[O:33])([CH2:16][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH:19]2[C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:17]=2)[CH2:14][NH:13]1)=[O:11]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86754402HCID 86754402, compound

Product 1

HCID 86754401HCID 86754401, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

467 mg (1 mmol) of (3aRS, 4SR, 9SR, 9aRS)-4,9-ethano-2-(2-methoxyphenyl)acetyl-9-phenyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-3a-carboxylic acid and 200 mg (1.2 mmol) of N,N'-carbonyldiimidazole are dissolved in 20 cm3 of dry dichloromethane. 10 cm3 of a 0.5N solution of ammonia in ethanol are then added and the mixture is then stirred for 16 hours at a temperature in the region of 20° C. After diluting with 50 cm3 of dichloromethane, the reaction mixture is washed successively, by separation by settling, with 50 cm3 of a 4N hydrochloric acid solution and then with 2 times 25 cm3 of a saturated sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The residue obtained is recrystallized from 13 cm3 of ethyl acetate. 350 mg (75%) of (3aRS, 4SR, 9SR, 9aRS)-4,9-ethano-2-(2-methoxyphenyl)acetyl-9-phenyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-3a-carboxamide are thus obtained in the form of white crystals, the characteristics of which are as follows: melting point=262-4° C., 1H N.M.R. spectrum (250 MHz, d6-(CD3)2SO, at a temperature of 383 K, δ in ppm): 1.36, 1.60, 1.88 and 2.05 (4 mts, each 1H, CH2CH2), from 3.20 to 3.65 (mt, 7H, CH2 at 1, COCH2Ar, 1H of the CH2 at 3, H at 4 and H at 9a), 3.67 (unresolved peak, 3H, OCH3), 4.22 (d, J=12.5 Hz, 1H, the other H of the CH2 at 3), 6.37 (broad d, J=7.5 Hz, 1H, H at 8), 6.75 (unresolved peak, 2H, CONH2), 6.88 (broad t, J=7.5 Hz, 1H, aromatic H para to the OCH3), 6.94 (broad d, J=7.5 Hz, 1H, aromatic H ortho to the OCH3), 7.02 (dt, J=7.5 and 2 Hz, 1H, H at 7), from 7.05 to 7.30 (mt, 4H, H at 5, H at 6 and aromatic H meta to the OCH3), 7.39 (mt, 3H, aromatic H in the ortho and para positions of the phenyl at 9), 7.48 (t, J=7.5 Hz, 2H, aromatic H in the meta positions of the phenyl at 9).

Workup

  1. washthe reaction mixture is washed successively, by separation
  2. dry with materialwith 2 times 25 cm3 of a saturated sodium chloride solution, dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customis recrystallized from 13 cm3 of ethyl acetate

Sources & evidence

ORD record
ord-d46497fdbfca495297c76055bd186b65
Source dataset
uspto-grants-1999_08
Patent number
US05936097

Reaction notes

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