Hydrochloric Acid → 1398695-47-0

HRID 880002Notes

Reaction equation

HRID 880002 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=2)[C:4]=1[C:18]1[CH:35]=[CH:34][C:21]2[CH2:22][CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][CH2:26][C:20]=2[CH:19]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=2)[C:4]=1[C:18]1[CH:35]=[CH:34][C:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:20]=2[CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 706650561,1-dimethylethyl 7-(2-(methyloxy)-6-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 601940981398695-47-0

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl 7-(2-(methyloxy)-6-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (2.57 g) was dissolved in dioxane (20 ml). Gaseous hydrogen chloride was passed through the reaction mixture for about 1.5 h. The reaction was monitored by TLC. On completion the solid formed was collected by filtration and washed with acetone. The solid was then dissolved in water and the mixture neutralised with aqueous sodium hydroxide (1M). The sticky solid formed was extracted with DCM. The organic phase was dried over sodium sulphate and concentrated in vacuo to give a solid. This was purified by silica column chromatography eluting with 0-8% methanol in DCM. The appropriate fractions were combined and concentrated in vacuo to yield a solid. This was triturated with diethyl ether to yield the title compound, 1.34 g (67%).

Workup

  1. customOn completion the solid formed
  2. filtrationwas collected by filtration
  3. washwashed with acetone
  4. dissolutionThe solid was then dissolved in water
  5. customThe sticky solid formed
  6. extractionwas extracted with DCM
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customto give a solid
  10. customThis was purified by silica column chromatography
  11. washeluting with 0-8% methanol in DCM
  12. concentrationconcentrated in vacuo
  13. customto yield a solid
  14. customThis was triturated with diethyl ether

Sources & evidence

ORD record
ord-b0a8e93f857349d9b9684a87d89222f8
Source dataset
uspto-grants-2015_03
Patent number
US08993560B2

Reaction notes

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