Hydroxide → HCID 86642595, compound

HRID 253751

Reaction equation

HRID 253751 reaction equation
[Cl:1]C1C=CC2OC3C=CC=CC=3[C@H]3C(=[O:13])N(C)C[C@@H]3C=2C=1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]2[O:37][C:36]3[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=3[C@@H:29]3[C:30](=[O:34])[N:31]([CH3:33])[CH2:32][C@@H:28]3[C:27]=2[CH:42]=1.[OH-]>C(O)C>[ClH:1].[Cl:22][C:23]1[CH:24]=[CH:25][C:26]2[O:37][C:36]3[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=3[C@@H:29]([C:30]([OH:34])=[O:13])[C@H:28]([CH2:32][NH:31][CH3:33])[C:27]=2[CH:42]=1

Participants

5

Reactant 3

HCID 961HydroxideHCID 56960600cis-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz-[2,3:6,7]oxepino[4,5-c]pyrrol-1-oneHCID 58729182(3aS,12bS)-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

Product 1

HCID 86642595HCID 86642595, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of lactams (VII) and (VIII) (13.6 grams, 45 mmol, trans/cis ratio 1:2.3), obtained as described under E, was dissolved in ethanol (140 ml). To the solution postassium hydroxide was added (43 grams, 811 mmol), whereupon the mixture was heated to reflux for 18 hours. Part of the ethanol (60 ml) was evaporated and water was added (200 mL). The aqueous phase was extracted twice with toluene (100 ml ). Subsequently toluene (100 ml) was added to the water phase, followed by concentrated hydrochloric acid to adjust the pH to 1. During the addition of hydrochloric acid the temperature rises to 75° C. The water layer was separated and upon cooling the product crystallized. The crystals were collected by filtration and dried to provide trans-2-chloro-10,11-dihydro-11[(methylamino)methy]-dibenz[b,f]oxepin-10-carboxylic acid hydrochloride (11)(3.75 grams, 10.6 mmol, 22%).

Workup

  1. customobtained
  2. temperaturewhereupon the mixture was heated
  3. temperatureto reflux for 18 hours
  4. customPart of the ethanol (60 ml) was evaporated
  5. additionwater was added (200 mL)
  6. extractionThe aqueous phase was extracted twice with toluene (100 ml )
  7. additionSubsequently toluene (100 ml) was added to the water phase
  8. additionDuring the addition of hydrochloric acid the temperature
  9. customrises to 75° C
  10. customThe water layer was separated
  11. temperatureupon cooling the product
  12. customcrystallized
  13. filtrationThe crystals were collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-26152e3b38f64fb19a4ccd3bf167916b
Source dataset
uspto-grants-2011_01
Patent number
US07872147B2

Linked notes

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