Lithium Hexamethyldisilazide → HCID 22464000, compound

HRID 1935324Notes

Reaction equation

HRID 1935324 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]#[N:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23].C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>C1C=CC=CC=1>[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][C:6]1([C:16]#[N:17])[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH2:9][CH2:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 1409111110,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile

Product 1

HCID 22464000HCID 22464000, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (100) (Med. Chem. Res. 1, 401 (1991)) (1.0 g, 4.56 mmol) and N-(2-chloroethyl)-N,N-dimethylamine hydrochloride (0.72 g, 5 mmol) in benzene (20 mL) was added 8.8 mL of a 1.3M solution of lithium hexamethyldisilazide (11.4 mmol). The mixture was heated at reflux under nitrogen for 18 hr and the solvent then removed under vacuum. The residue was treated with water (20 mL) and extracted twice with methylene chloride (20 mL). The organic layers were combined, dried over sodium sulfate, and chromatographed directly on silica gel eluted with methylene chloride followed by 95:5:0.5, then 90:10:1 methylene chloride:methanol:ammonium hydroxide. The product fractions were evaporated to dryness in vacuo to give the title compound as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for 18 hr
  3. customthe solvent then removed under vacuum
  4. additionThe residue was treated with water (20 mL)
  5. extractionextracted twice with methylene chloride (20 mL)
  6. dry with materialdried over sodium sulfate
  7. customchromatographed directly on silica gel
  8. washeluted with methylene chloride
  9. customThe product fractions were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-376fe045a93544238ec480c2bfad6350
Source dataset
uspto-grants-2002_05
Patent number
US06387893B1

Reaction notes

Loading…