4-Fluorobenzoyl chloride → HCID 11326136, compound

HRID 1661175Notes

Reaction equation

HRID 1661175 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[F:12][C:13]1[CH:14]=[C:15]([C:19]2[N:23]=[C:22]([CH:24]3[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]3)[O:21][N:20]=2)[CH:16]=[CH:17][CH:18]=1>C(Cl)Cl.CO>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:26]2[CH2:27][CH2:28][CH2:29][CH:24]([C:22]3[O:21][N:20]=[C:19]([C:15]4[CH:16]=[CH:17][CH:18]=[C:13]([F:12])[CH:14]=4)[N:23]=3)[CH2:25]2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 470029631235441-45-8

Product 1

HCID 11326136HCID 11326136, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The compound was prepared following the procedure described in the Example 3 (D), using 4-Fluoro-benzoyl chloride as the acyl chloride of choice and the 3-[3-(3-Fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidine hydrochloride (already prepared before in the Example 9). Yield: 50% (yellow oil); Mp=86-89° C. (beige powder); Rf=0.28 (DCM/MeOH: 98/2); LCMS (Tr): 4.88 min (Method C); MS (ES+) gave m/z: 370.3; 1H-NMR (CDCl3), δ (ppm): 8.05-7.90 (m, 2H), 7.30-7.23 (m, 2H), 7.25-7.15 (m, 3H), 7.00 (m, 1H), 3.65-3.32 (m, 4H), 2.53 (m, H), 1.86-1.45 (m, 4H).

Workup

  1. customThe compound was prepared
  2. custom4.88 min (Method C)
  3. customMS (ES+) gave m/z

Sources & evidence

ORD record
ord-b250e29843724fd2befa585fb5dba5ff
Source dataset
uspto-grants-2011_10
Patent number
US08030331B2

Reaction notes

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