4-Fluorobenzoyl chloride → HCID 57893758, compound

HRID 1822025Notes

Reaction equation

HRID 1822025 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=1[O:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1>N1C=CC=CC=1.C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][C:15]2[CH:16]=[CH:17][C:12]([CH3:11])=[C:13]([O:19][CH:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[CH:14]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 450976834-Methyl-3-[(1-methylpiperidin-4-yl)oxy]aniline

Product 1

HCID 57893758HCID 57893758, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Add 4-fluorobenzoyl chloride (222 mg, 1.4 mmol) to a solution of 4-Methyl-3-(1-methyl-piperidin-4-yloxy)-phenylamine (preparation 34, 280 mg, 1.27 mmol) in pyridine (10 mL), beat at 55° C. for 20 hr. Remove volatiles in vacuo, dissolve the residue in CH2Cl2, wash with 0.1N NaOH and saturated NaCl solution sequentially, dry over Na2SO4, filter and concentrate to give a residue. Chromatography on a silica gel column eluting with 6% 2M NH3-methanol in CH2Cl2) provides the title compound as a colorless oil (375 mg, 86%). Mass spectrum (ion spray): m/z=343.3 (M+1); 1H NMR (CDCl3, ppm): 7.94 (s, br, 1H), 7.88 (m, 2H), 7.85 (s, br, 1H), 7.12 (m, 3H), 6.87 (dd, 1H), 4.39 (m, 1H), 2.62 (m, 2H), 2.33 (m, 2H), 2.31 (s, 3H), 2.22 (s, 3H), 2.06-1.83 (m, 4H); Anal calcd for C20H23FN2O2.HCl H2O: C, 60.53; H, 6.60; N, 7.06. Found: C, 60.77; H, 6.20; N, 7.10.

Workup

  1. washwash with 0.1N NaOH and saturated NaCl solution sequentially
  2. dry with materialdry over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customto give a residue
  6. washChromatography on a silica gel column eluting with 6% 2M NH3-methanol in CH2Cl2)

Sources & evidence

ORD record
ord-ee990cc3108a45a09c94b667933828aa
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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