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

HRID 880005Notes

Reaction equation

HRID 880005 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:28][CH2:29][C:30]2[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][N:31]=2)=[C:8]([C:10]2[CH:27]=[CH:26][C:13]3[CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18][C:12]=3[CH:11]=2)[CH:9]=1)(=[O:3])[CH3:2].Cl>O1CCOCC1>[CH3:36][C:34]1[CH:33]=[CH:32][N:31]=[C:30]([CH2:29][O:28][C:7]2[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:9][C:8]=2[C:10]2[CH:27]=[CH:26][C:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18][C:12]=3[CH:11]=2)[CH:35]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 706652371,1-dimethylethyl 7-(5-acetyl-2-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 706650591-[4-{[(4-methyl-2-pyridinyl)methyl]oxy}-3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl 7-(5-acetyl-2-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (3.0 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 neutralised with aqueous sodium hydroxide (1M). Solid was obtained which was collected by filtration. This was triturated with diethyl ether to yield the title compound, 2.1 g (88%).

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. customSolid was obtained which
  6. filtrationwas collected by filtration
  7. customThis was triturated with diethyl ether

Sources & evidence

ORD record
ord-215439c87c5f412da46b72f8ed9f140c
Source dataset
uspto-grants-2015_03
Patent number
US08993560B2

Reaction notes

Loading…