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

HRID 63288Notes

Reaction equation

HRID 63288 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH2:27][C:28]2[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][N:29]=2)=[C:6]([C:8]2[CH:25]=[CH:24][C:11]3[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH2:16][C:10]=3[CH:9]=2)[CH:7]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH2:27][C:28]2[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][N:29]=2)=[C:6]([C:8]2[CH:25]=[CH:24][C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:10]=3[CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 706649671,1-dimethylethyl 7-(5-fluoro-2-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 706653717-(5-fluoro-2-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1,1-dimethylethyl 7-(5-fluoro-2-{[(4-methyl-2-pyridinyl)methyl]oxy}phenyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate, (0.304 g) was dissolved in a minimum amount of dioxane. The solution was cooled in ice and to this was added a solution of HCl in dioxane (2 ml). This was stirred until the reaction had gone to completion by tlc. The reaction mixture was concentrated in vacuo. The product salt was dissolved in water and backwashed with ethyl acetate. The aqueous was neutralised with aqueous sodium hydroxide (1M). This was extracted with ethyl acetate. The organics were dried over sodium sulphate and concentrated to give the title compound, 100 mg.

Workup

  1. temperatureThe solution was cooled in ice
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe product salt was dissolved in water
  4. extractionThis was extracted with ethyl acetate
  5. dry with materialThe organics were dried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c38be5ebcfcc4aeab62dfe3a7066a3cc
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Reaction notes

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