Hydrochloric Acid → 8-(4-(Aminomethyl)phenyl)-2-morpholino-4H-chromen-4-one

HRID 1626719Notes

Reaction equation

HRID 1626719 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[O:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:21][C:20]3=[O:31])=[CH:11][CH:10]=1)(C)(C)C.Cl>ClCCl.O1CCOCC1>[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[O:23][C:22]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)=[CH:21][C:20]3=[O:31])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66685659[4-(2-morpholin-4-yl-4-oxo-4H-chromen-8-yl)-benzyl]-carbamic acid tert-butyl ester

Product 1

HCID 569322398-(4-(Aminomethyl)phenyl)-2-morpholino-4H-chromen-4-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

[4-(2-Morpholin-4-yl-4-oxo-4H-chromen-8-yl)-benzyl]-carbamic acid tert-butyl ester [F] (230 mg, 0.53 mmol), in dichloromethane (5 ml) was treated with 4M hydrogen chloride in dioxane (2 ml). The reaction was stirred at room temperature for 3 hours during which time a precipitate forms. The solvent was removed in vacuo and the residue triturated with ether. The resulting solid was collected by filtration and dried to give 8-(4-aminomethyl-phenyl)-2-morpholin-4-yl-chromen-4-one [G]. Yield 189 mg, quantitative.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue triturated with ether
  3. filtrationThe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-e0585963606f47f685036c8d3d4cc17f
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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