Propargyl bromide → HCID 13315028, compound

HRID 1863486Notes

Reaction equation

HRID 1863486 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([CH:7]=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)[CH2:2]1.[CH2:23](Br)[C:24]#[CH:25].[OH-].[K+]>C(O)C.O>[CH2:25]([N:1]1[CH2:6][CH2:5][O:4][CH:3]([CH:7]=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)[CH2:2]1)[C:24]#[CH:23]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 14797Potassium HydroxideHCID 13308996HCID 13308996, compound

Product 1

HCID 13315028HCID 13315028, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 5-(morpholin-2-yl)methylidene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (300 mg) in ethanol were added propargyl bromide (2.0 g) and potassium hydroxide (570 mg) in water at room temperature, and the resulting mixture was stirred at room temperature for 1 hour. After ethanol was distilled off, water was added to the residue, and the resultant mixture was extracted with chloroform. The chloroform extract was dried, evaporated and chromatographed to afford 5-(4-propargylmorpholin-2-yl)methylidene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as crystalline material. M.P., 124°-125° C.

Workup

  1. distillationAfter ethanol was distilled off
  2. additionwater was added to the residue
  3. extractionthe resultant mixture was extracted with chloroform
  4. extractionThe chloroform extract
  5. customwas dried
  6. customevaporated
  7. customchromatographed

Sources & evidence

ORD record
ord-134db75bbeea4e99a5cf4bdd127f7025
Source dataset
uspto-grants-1979_09
Patent number
US04169146

Reaction notes

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