Hydrochloric Acid → HCID 22732530, compound

HRID 1765155Notes

Reaction equation

HRID 1765155 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:3]=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1.Cl.[OH-].[Na+]>O.C(O)C>[O:17]1[CH2:18][CH2:19][N:14]([C:4]2[N:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:7]=[C:2]([NH:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH3:20])[CH:23]=3)[CH:3]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108243-MethoxyanilineHCID 14798Sodium HydroxideHCID 11019114-(6-chloro-2-phenyl-4-pyrimidinyl)morpholine

Product 1

HCID 22732530HCID 22732530, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-(6-chloro-2-phenyl-4-pyrimidyl)morpholine (50 mg, 0.181 mmol), m-anisidine (20 μl, 0.181 mmol) and aqueous 2N HCl (150 μl) in water:ethanol (1:1, 10 ml) was refluxed for 5 days. The mixture was cooled to room temperature and basified with aqueous 2N NaOH to pH 10–12. The mixture was extracted with ethyl acetate (50 ml), which was washed with water (2×25 ml), aqueous saturated NaCl, and dried over anhydrous sodium sulfate. The ethyl acetate solution was concentrated in vacuo and isolated as a yellow solid (6 mg, 9%). 1H NMR (CDCl3): 8.40–8.37 (m, 2H), 7.46–7.43 (m, 3H), 7.31–7.25 (m, 2H), 7.00 (t, J=2.3 Hz, 1H), 6.91 (dd, J=1.7, 8.0 Hz, 1H), 6.70–6.67 (m, 2H), 3.83 (s, 3H), 3.81–3.63 (m, 8H).

Workup

  1. temperaturewas refluxed for 5 days
  2. extractionThe mixture was extracted with ethyl acetate (50 ml), which
  3. washwas washed with water (2×25 ml), aqueous saturated NaCl
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe ethyl acetate solution was concentrated in vacuo

Sources & evidence

ORD record
ord-fc165ca273c848bb974307eff2bfb435
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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