Triethylamine → HCID 86753436, compound

HRID 1457682Notes

Reaction equation

HRID 1457682 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH2:8]([O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)[CH2:9][CH2:10][CH3:11].[OH-].[Na+]>C(Cl)Cl>[CH3:11][CH2:10][CH2:9][CH2:8][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([C:8]2[C:7]3[CH2:16][C:15]4[CH:14]=[CH:13][CH:21]=[CH:20][C:5]=4[CH2:4][NH:3][C:6]=3[CH:11]=[CH:10][CH:9]=2)=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 1185614-Butoxybenzoyl chloride

Product 1

HCID 86753436HCID 86753436, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,11-dihydro-5H-dihydro-5H-dibenz[b,e]azepine (0.12 g, 0.6 mmol) in methylene chloride (2 ml) is added triethylamine (0.12 g, 1.2 mmol), followed by 4-butoxybenzoyl chloride ((0.15 g, 0.72 mmol). The resulting mixture is stirred at room temperature for 2 hours, and then treated with 4 ml of 1N NaOH. The mixture is extracted with ethyl acetate (10 ml), and the extract is washed with 1N sodium hydroxide and brine (5 ml), dried over anhydrous sodium sulfate, and filtered through hydrous magnesium silicate. The filtrate is evaporated, and the crude material is triturated with isoctane to give 0.24 g of white solid; Mass spectrum (CI), 372(MH+)

Workup

  1. extractionThe mixture is extracted with ethyl acetate (10 ml)
  2. washthe extract is washed with 1N sodium hydroxide and brine (5 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through hydrous magnesium silicate
  5. customThe filtrate is evaporated
  6. customthe crude material is triturated with isoctane

Sources & evidence

ORD record
ord-38b0a40c001643cbbde24aff1ed6d839
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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