Triethylsilane → HCID 17848741, compound

HRID 1766005Notes

Reaction equation

HRID 1766005 reaction equation
C([SiH](CC)CC)C.[C:8]([N:11]1[C:17]2[CH:18]=[C:19]([C:22](=O)[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH:20]=[CH:21][C:16]=2[CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:10])[CH3:9]>FC(F)(F)C(O)=O>[C:8]([N:11]1[C:17]2[CH:18]=[C:19](/[CH:22]=[CH:23]/[CH2:24][N:25]([CH3:27])[CH3:26])[CH:20]=[CH:21][C:16]=2[CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 17848835HCID 17848835, compound

Product 1

HCID 17848741HCID 17848741, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethyl silane (22.2 ml, 139 mmol) was added under a nitrogen atmosphere to a solution of 1-(1-acetyl-2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-3-(dimethylamino)-1-propanone (5.00 g, 17.3 mmol) obtained in Reference Example 8 in trifluoroacetic acid, and then the mixture was stirred at room temperature for 5 days. After the solvent was distilled away under reduced pressure, ether was added to the residues which were then extracted with water. The aqueous layer was made basic with 8 N aqueous sodium hydroxide and then extracted with ethyl acetate. The extract was washed with a saturated saline solution and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=1:1), whereby the title compound (2.74 g) was obtained as oily matter.

Workup

  1. distillationAfter the solvent was distilled away under reduced pressure, ether
  2. additionwas added to the residues which
  3. extractionwere then extracted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated saline solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=1:1), whereby the title compound (2.74 g)
  9. customwas obtained as oily matter

Sources & evidence

ORD record
ord-6c3235e1bd4e469fa0a2c45503630d22
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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