Hydrochloric Acid → (Z)-3-amino-4,4-dimethyl-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-one

HRID 529477Notes

Reaction equation

HRID 529477 reaction equation
[CH3:1][C:2]1([CH3:24])[CH:3]([NH:16]C(=O)OC(C)(C)C)[C:4](=[O:15])[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH:7]=[CH:8]1.Cl>O1CCOCC1>[NH2:16][CH:3]1[C:2]([CH3:24])([CH3:1])[CH:8]=[CH:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4]1=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 68292253(Z)-tert-butyl 4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

Product 1

HCID 68292320(Z)-3-amino-4,4-dimethyl-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a round bottom flask was added (Z)-tert-butyl 4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (7 mg, 0.02 mmol) and 4 N HCl in dioxane (1 mL). The reaction was stirred at rt for 1 hr. The solvent was removed to give (Z)-3-amino-4,4-dimethyl-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-one (4 mg, 0.02 mmol, 82% yield) as mono hydrochloride salt. Anal. Calcd. for C14H18N2O m/z 230.2. found: 231.2 (M+H)+.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-4d10bdb4fc8b4985a64b09930db813d1
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

Loading…