Hydrochloric Acid → (S)-3-amino-1-(3-chlorophenyl)azepan-2-one hydrochloride

HRID 529516Notes

Reaction equation

HRID 529516 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]([NH:15]C(=O)OC(C)(C)C)[C:9]2=[O:23])[CH:5]=[CH:6][CH:7]=1.Cl.O1CCOCC1>C(Cl)Cl>[ClH:1].[NH2:15][C@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:9]1=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68310942(S)-tert-butyl 1-(3-chlorophenyl)-2-oxoazepan-3-ylcarbamate

Product 1

HCID 68291572(S)-3-amino-1-(3-chlorophenyl)azepan-2-one hydrochlorideYield 196%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-tert-butyl 1-(3-chlorophenyl)-2-oxoazepan-3-ylcarbamate (35 mg, 0.10 mmol) in DCM (2 mL) was added 4.0 M HCl in dioxane (0.258 mL, 1.03 mmol) at rt under argon. The reaction was stirred at rt for 6 hr. The reaction mixture was concentrated and dried under vacuum to give (S)-3-amino-1-(3-chlorophenyl)azepan-2-one hydrochloride (27 mg, 0.098 mmol, 95% yield) as white solid. Anal. Calcd. for C12H15ClN2O m/z 238.2. found: 239.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-2118b057ba134bcfab1cda4f3878f461
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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