HCID 90041922, compound → HCID 90042217, compound

HRID 530380Notes

Reaction equation

HRID 530380 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-])=O>C(OCC)(=O)C.C(O)(=O)C.ClCCl.[Pd]>[N:16]1([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=2)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1

Participants

6

Reactant 1

HCID 90041922HCID 90041922, compound

Product 1

HCID 90042217HCID 90042217, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pd/C (53.9 mg, 0.051 mmol) was added to a solution of 4-(5-nitrobiphenyl-3-yl)morpholine (144 mg, 0.506 mmol) in ethyl acetate (5 mL) and acetic acid (0.5 mL). The reaction mixture was stirred under H2 atmosphere (1 atm) for 2 hours at room temperature. The reaction mixture was diluted with dichloromethane and filtered through CELITE and washed with ethyl acetate. The resultant solution was concentrated in vacuo to provide 5-(morpholin-4-yl)biphenyl-3-amine as a grey solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.57 (d, J=5.7 Hz, 2H), 7.36 (dd, J=32.4, 26.2 Hz, 3H), 6.58 (s, 1H), 6.49 (s, 1H), 6.27 (s, 1H), 5.13 (s, 2H), 3.89 (s, 4H), 3.21 (s, 4H).

Workup

  1. filtrationfiltered through CELITE
  2. washwashed with ethyl acetate
  3. concentrationThe resultant solution was concentrated in vacuo

Sources & evidence

ORD record
ord-9964944dfae84a969fc43a1263f2893a
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

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