Water → HCID 22396201, compound

HRID 1070508Notes

Reaction equation

HRID 1070508 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:10])=[CH:4][CH:3]=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:15]2[CH2:16][CH2:17][CH:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:13][CH2:14]2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 16788635HCID 16788635, compound

Product 1

HCID 22396201HCID 22396201, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Fluorophenyl)-N-(4-piperidinyl)acetamide (WO97/36871; 1.00 g), 1-bromo-4-(bromomethyl)benzene (1.06 g) and potassium carbonate (0.877 g) in dimethylformamide (15 ml) were heated to 70° C., under nitrogen for 1 hour. Water was added to the reaction, with the resulting solution being extracted three times with dichloromethane. The pooled organic phases were washed once with water, once with brine, dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to leave a cream solid. This solid was triturated with diethyl ether, filtered and recrystallised from ethanol/water to give water crystalline needles of N-[1-(4-bromobenzyl)-4-piperidinyl]-2-(4-fluorophenyl)acetamide. m.p. (+veES) 407 ((M+H)+)

Workup

  1. extractionbeing extracted three times with dichloromethane
  2. washThe pooled organic phases were washed once with water, once with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto leave a cream solid
  7. customThis solid was triturated with diethyl ether
  8. filtrationfiltered
  9. customrecrystallised from ethanol/water

Sources & evidence

ORD record
ord-ba99ed33b02c4666bfaadb27e48995ce
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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