Hydrochloric Acid → 7-(3-{[(4-ethyl-2-pyridinyl)methyl]oxy}-6-methyl-2-pyridinyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 880009Notes

Reaction equation

HRID 880009 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][C:11]2[C:12]([C:18]3[CH:35]=[CH:34][C:21]4[CH2:22][CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][CH2:26][C:20]=4[CH:19]=3)=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[CH:4]=1)[CH3:2].Cl>O1CCOCC1>[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][C:11]2[C:12]([C:18]3[CH:35]=[CH:34][C:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:20]=4[CH:19]=3)=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 706651171,1-dimethylethyl 7-(3-{[(4-ethyl-2-pyridinyl)methyl]oxy}-6-methyl-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 706653747-(3-{[(4-ethyl-2-pyridinyl)methyl]oxy}-6-methyl-2-pyridinyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1,1-dimethylethyl 7-(3-{[(4-ethyl-2-pyridinyl)methyl]oxy}-6-methyl-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate, (4.3 g) in dioxane (30 ml) was passed through HCl (gas) for 30 min at 20° C. After completion of reaction by TLC, the solvent was removed in vacuo. The solid obtained was washed with acetone and dissolved in water. This was neutralised with sodium bicarbonate, extracted with DCM and concentrated in vacuo to give a crude product. This was purified through silica using 6% methanol in DCM. Appropriate fractions were combined and concentrated in vacuo to give a product. This was triturated in diethyl ether to yield the title compound, 1.5 g.

Workup

  1. customAfter completion of reaction by TLC
  2. customthe solvent was removed in vacuo
  3. customThe solid obtained
  4. washwas washed with acetone
  5. dissolutiondissolved in water
  6. extractionextracted with DCM
  7. concentrationconcentrated in vacuo
  8. customto give a crude product
  9. customThis was purified through silica using 6% methanol in DCM
  10. concentrationconcentrated in vacuo
  11. customto give a product
  12. customThis was triturated in diethyl ether

Sources & evidence

ORD record
ord-a2a3eb8d349b47098c7541cdeecd008e
Source dataset
uspto-grants-2015_03
Patent number
US08993560B2

Reaction notes

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