Hydrochloric Acid → HCID 59828832, compound

HRID 2041254Notes

Reaction equation

HRID 2041254 reaction equation
[CH3:1][C:2]1([C:7]2[CH:32]=[CH:31][C:10]([CH2:11][NH:12][C:13]3[C:23]4[CH2:22][CH2:21][N:20]([C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH2:19][CH2:18][C:17]=4[CH:16]=[CH:15][C:14]=3[Cl:30])=[CH:9][CH:8]=2)OCC[O:3]1.Cl>CO>[C:2]([C:7]1[CH:8]=[CH:9][C:10]([CH2:11][NH:12][C:13]2[C:23]3[CH2:22][CH2:21][N:20]([C:24](=[O:29])[C:25]([F:27])([F:28])[F:26])[CH2:19][CH2:18][C:17]=3[CH:16]=[CH:15][C:14]=2[Cl:30])=[CH:31][CH:32]=1)(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59828873HCID 59828873, compound

Product 1

HCID 59828832HCID 59828832, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 6-{4-(2-methyl-[1,3]dioxolan-2-yl)benzylamino}-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (150 mg, 0.32 mmol) in methanol (5 mL) and add 1N aqueous HCl (1 mL). Stir the solution at ambient temperature for 2 h. Remove the solvent, dissolve the residue in DCM and wash with saturated aqueous NaHCO3. Dry the organic phase over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 17:3 and 4:1) to obtain 6-(4-acetyl-benzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil (107 mg, 79%). GC-MS m/z 424 (M+).

Workup

  1. customRemove the solvent
  2. dissolutiondissolve the residue in DCM
  3. washwash with saturated aqueous NaHCO3
  4. dry with materialDry the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 17:3 and 4:1)

Sources & evidence

ORD record
ord-4b7ab8f9f67a4377a10e8125e9cbe7d5
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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