Sodium Hydroxide → HCID 54456995, compound

HRID 366773Notes

Reaction equation

HRID 366773 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:29]=[CH:28][C:7]2[C:8](=[C:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:9]3[C:14]([CH2:15][O:16][C:6]=2[CH:5]=1)=[CH:13][CH:12]=[CH:11][N:10]=3.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:29]1[C:4]([Cl:3])=[CH:5][C:6]2[O:16][CH2:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[C:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:7]=2[CH:28]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 15341448HCID 15341448, compound

Product 1

HCID 54456995HCID 54456995, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Bromine (0.5 ml, 9.7 mmol) was added to a solution of ethyl 4-(8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)-1-piperidine-carboxylate (1.0 g., 2.6 mmol) in methylene chloride (15 ml) at 20° C. The solution was stirred for 2 hours at 20° C. The reaction mixture was poured onto ice (50 g), basified with 10% NaOH, and extracted with methylene chloride (100 ml). The organic layer was separated, washed with water (20 ml), dried (MgSO4), filtered and evaporated, yielding an oil which was chromatographed on silica gel and eluted with 1:1 ethylacetate/hexanes. The product, ethyl 4-(9-bromo-8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ylidene)-1-piperidine-carboxylate (0.8 g., 66% yield) was obtained as a white solid; MS (CI, M+H)=465.

Workup

  1. additionThe reaction mixture was poured onto ice (50 g)
  2. extractionextracted with methylene chloride (100 ml)
  3. customThe organic layer was separated
  4. washwashed with water (20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customyielding an oil which
  9. customwas chromatographed on silica gel
  10. washeluted with 1:1 ethylacetate/hexanes

Sources & evidence

ORD record
ord-e7eec8ec048a423abe045ff81aeba44f
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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