Sodium Hydroxide → 7-chloro-6-(3-fluoro-4-methoxycarbonyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 2041494Notes

Reaction equation

HRID 2041494 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:20]=[CH:19][C:7]2[CH2:8][CH2:9][N:10](C(=O)C(F)(F)F)[CH2:11][CH2:12][C:6]=2[C:5]=1[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[C:25]([F:33])[CH:24]=1>O1CCOCC1.O>[Cl:3][C:4]1[CH:20]=[CH:19][C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[C:5]=1[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[C:25]([F:33])[CH:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 576561377-Chloro-6-(3-fluoro-4-methoxycarbonyl-benzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 576563327-chloro-6-(3-fluoro-4-methoxycarbonyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 1M aqueous NaOH (2.8 mL, 2.8 mmol) to a solution of 7-chloro-6-(3-fluoro-4-methoxycarbonyl-benzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.31 g, 2.86 mmol) in 1,4-dioxane (13.3 mL) and water (2.6 mL) at 11° C. Allow mixture to warm to room temperature and stir for 1 h. Concentrate in vacuo and partition the residue between dichloromethane (250 mL) and saturated aqueous NaHCO3 (100 mL). Dry the organic phase over Na2SO4, filter and concentrate in vacuo to afford the desired intermediate that was used without further purification.

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition the residue between dichloromethane (250 mL) and saturated aqueous NaHCO3 (100 mL)
  3. dry with materialDry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-ce82da8a8e10430993d861f9710c9c2f
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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