Dichloromethane → HCID 90041742, compound

HRID 530383Notes

Reaction equation

HRID 530383 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-])=O.[H][H].ClCCl>[Pd].C(OCC)(=O)C.C(O)(=O)C>[N:17]1([CH2:16][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)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 90042177HCID 90042177, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90041742HCID 90041742, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon (10 wt %, 47.8 mg, 0.045 mmol) was added to a solution of 4-[(5-nitrobiphenyl-3-yl)methyl]morpholine in ethyl acetate (4.1 mL) and acetic acid (0.408 mL). The reaction mixture was fitted with a hydrogen balloon and stirred at room temperature for 3 hours. Dichloromethane was added to the reaction mixture, and then filtered through CELITE and washed with dichloromethane. The organic fractions were washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 5-(morpholin-4-ylmethyl)biphenyl-3-amine which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.58 (t, J=5.9 Hz, 2H), 7.43 (dd, J=9.5, 5.6 Hz, 2H), 7.35 (t, J=7.3 Hz, 1H), 6.97 (s, 1H), 6.83 (s, 1H), 6.71 (s, 1H), 3.92-3.61 (m, 4H), 3.49 (s, 2H), 2.50 (s, 4H).

Workup

  1. filtrationfiltered through CELITE
  2. washwashed with dichloromethane
  3. washThe organic fractions were washed with saturated aqueous NaHCO3
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39b88ee397f24c42b5282757deef02ec
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

Loading…