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

HRID 63284Notes

Reaction equation

HRID 63284 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:26]=[CH:25][C:12]3[CH2:13][CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16][CH2:17][C:11]=3[CH:10]=2)=[C:5]([O:27][CH2:28][C:29]2[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][N:30]=2)[CH:4]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:26]=[CH:25][C:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17][C:11]=3[CH:10]=2)=[C:5]([O:27][CH2:28][C:29]2[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][N:30]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 706650231,1-dimethylethyl 7-(4-(methyloxy)-2-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 706652417-(4-(methyloxy)-2-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl 7-(4-(methyloxy)-2-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (4.8 g) was dissolved in dioxane (20 ml). Gaseous hydrogen chloride was passed through the reaction mixture for 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 was brought to pH8 using aqueous sodium bicarbonate. The sticky solid observed was extracted with DCM. The organics were dried over sodium sulphate and concentrated in vacuo to yield a solid. This was purified by column chromatography eluting with 0-8% methanol in DCM. Appropriate fractions were combined and concentrated in vacuo to yield a solid. This was triturated in diethyl ether to yield the title compound, 1.7 g (45%).

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. extractionThe sticky solid observed was extracted with DCM
  6. dry with materialThe organics were dried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customto yield a solid
  9. customThis was purified by column chromatography
  10. washeluting with 0-8% methanol in DCM
  11. concentrationconcentrated in vacuo
  12. customto yield a solid
  13. customThis was triturated in diethyl ether

Sources & evidence

ORD record
ord-977e2d2a58fd4811941e7e941fafc4a6
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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