Triethylamine → 2-{3-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]propyl}-1H-isoindole-1,3(2H)-dione

HRID 496893

Reaction equation

HRID 496893 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.Br[CH2:17][CH2:18][CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:17][CH2:18][CH2:19][N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21611N-3-BromopropylphthalimideHCID 37320424-(3,4-Dichlorophenoxy)piperidine

Product 1

HCID 223223692-{3-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]propyl}-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Example 1 step (ii) (2.0 g), 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione (1.61 g) and triethylamine (2.5 ml) in dichloromethane (40 ml) was heated under reflux for 48 h. The reaction mixture was partitioned between ethyl acetate/water, the organic layer dried and evaporated under reduced pressure. Purification was by chromatography eluting with 4% methanol/dichloromethane. Yield 0.839 g

Workup

  1. temperatureunder reflux for 48 h
  2. customThe reaction mixture was partitioned between ethyl acetate/water
  3. customthe organic layer dried
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-350f6e33c65941ed80067085fafafb90
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Linked notes

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