Hydrochloric Acid → 3-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride

HRID 634413Notes

Reaction equation

HRID 634413 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19])[O:3]1.[ClH:28].O1CCOCC1>C(Cl)Cl>[ClH:28].[NH2:20][CH:18]([C:4]1[O:3][C:2](=[O:1])[C:11]2[C:6]([C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118131293tert-butyl 1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethylcarbamate2×

Product 1

HCID 1181314633-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethylcarbamate (Intermediate E1, 112 mg, 0.306 mmol) was dissolved in DCM (3 ml), then a solution of 4M HCl in dioxane (3 ml, 12.00 mmol) was added and the mixture stirred rt for 4 h. The reaction was quenched by the addition of Et2O (50 mL) and the mixture dried under reduced pressure to afford the title compound.

Workup

  1. customThe reaction was quenched by the addition of Et2O (50 mL)
  2. customthe mixture dried under reduced pressure

Sources & evidence

ORD record
ord-910effec27f94e77b08c2d88fec60dcb
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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