1,2-Difluorobenzene → HCID 54574047, compound

HRID 344461Notes

Reaction equation

HRID 344461 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:9])=[C:6]([O:21][CH3:22])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([C:37]1[CH:42]=[CH:41][C:40]([F:43])=[C:39]([F:44])[CH:38]=1)=[O:36].BrCCCCCC(Cl)=O.FC1C=CC=CC=1F>>[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[C:39]([F:44])[CH:38]=3)=[O:36])[CH2:16][CH2:17]2)=[O:9])=[C:6]([O:21][CH3:22])[CH:5]=1

Participants

6

Reactant 5

HCID 97061,2-DifluorobenzeneHCID 11430Potassium CarbonateHCID 898486-Bromohexanoyl chlorideHCID 53698228HCID 53698228, compoundHCID 699663304-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride

Product 1

HCID 54574047HCID 54574047, compoundYield 28.7%

Procedure

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (0.57 g) as starting compound, potassium carbonate (0.82 g), and 6-bromo-1-(3,4-difluorophenyl)-1-hexanone (0.42 g) obtained by subjecting 6-bromohexanoyl chloride and 1,2-difluorobenzene to Friedel-Crafts reaction were reacted and treated in the same manner as in Example 172 to give 0.21 g of 4-amino-5-chloro-N-((1-(6-(3,4-difluorophenyl)-6-oxohexyl)piperidin-4-yl)methyl)-2-methoxybenzamide.

Workup

  1. customobtained
  2. customto Friedel-Crafts reaction
  3. customwere reacted
  4. additiontreated in the same manner as in Example 172

Sources & evidence

ORD record
ord-9058f4c226fe4b7cb881bf264b7d1be7
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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