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

HRID 880007Notes

Reaction equation

HRID 880007 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[CH:34]=[CH:33][C:20]3[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C:19]=3[CH:18]=2)[CH:4]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[CH:34]=[CH:33][C:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:19]=3[CH:18]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 706650151,1-dimethylethyl 7-[2-({[4-(methyloxy)-2-pyridinyl]methyl}oxy)phenyl]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 706653917-[2-({[4-(methyloxy)-2-pyridinyl]methyl}oxy)phenyl]-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-[2-({[4-(methyloxy)-2-pyridinyl]methyl}oxy)phenyl]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (3.0 g) in dioxane (30 ml) was added hydrogen chloride gas for 2 h at 10-20° C. This was concentrated in vacuo. The residue was dissolved in water, washed with ethyl acetate and basified by adding aqueous sodium bicarbonate. This was extracted with 10% methanol in DCM. The organics were dried over sodium sulphate and concentrated in vacuo to yield the title compound, 2.14 g (91%).

Workup

  1. concentrationThis was concentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. washwashed with ethyl acetate
  4. additionby adding aqueous sodium bicarbonate
  5. extractionThis was extracted with 10% methanol in DCM
  6. dry with materialThe organics were dried over sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbffb0965fa6454a89c36daf32db5446
Source dataset
uspto-grants-2015_03
Patent number
US08993560B2

Reaction notes

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