Triethylamine → 4-Chloro-N-{2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}-2-[2-(dimethylamino)-2-oxoethoxy]benzamide

HRID 496872Notes

Reaction equation

HRID 496872 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.FC(F)(F)C(O)=O.[Cl:37][C:38]1[CH:39]=[C:40]([CH:51]=[CH:52][C:53]=1[Cl:54])[O:41][CH:42]1[CH2:47][CH2:46][N:45]([CH2:48][CH2:49][NH2:50])[CH2:44][CH2:43]1.C(N(CC)CC)C>CN(C=O)C.CCOCC.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:50][CH2:49][CH2:48][N:45]2[CH2:46][CH2:47][CH:42]([O:41][C:40]3[CH:51]=[CH:52][C:53]([Cl:54])=[C:38]([Cl:37])[CH:39]=3)[CH2:43][CH2:44]2)=[O:8])=[C:4]([O:11][CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 112539014-Chloro-2-[2-(dimethylamino)-2-oxoethoxy]benzoic acidHCID 223224532-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethylamine trifluoroacetate

Product 1

HCID 99585994-Chloro-N-{2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}-2-[2-(dimethylamino)-2-oxoethoxy]benzamideYield 69%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

The product from step (vi) (0.3 g) and N,N-carbonyldiimidazole (0.19 g) were dissolved in DMF (20 ml) and the solution stirred at room temperature for 1 hour. The product from step (iv) (0.42 g) and triethylamine (0.32 ml) were added. After 20 hours water and ether were added, the organic phase separated, dried and concentrated to a gum which was purified by chromatography (dichloromethane:methanol, 93:7) to give the titled product as a solid (0.38 g).

Workup

  1. customthe organic phase separated
  2. customdried
  3. concentrationconcentrated to a gum which
  4. customwas purified by chromatography (dichloromethane:methanol, 93:7)

Sources & evidence

ORD record
ord-37b80cb4bcc24f54a493814ac3d818fe
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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