Hydrochloric Acid → HCID 22732530, compound

HRID 2084101Notes

Reaction equation

HRID 2084101 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-f65e567069574c29881ff05bf7768602
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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