Dimethylformamide → (S)-2-[3-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione

HRID 2233366Notes

Reaction equation

HRID 2233366 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[NH:2]1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:16]N1CCCCC1.[CH3:27][N:28]([CH:30]=O)[CH3:29]>C(O)C>[Cl:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:16][CH:6]1[CH2:7][CH2:29][N:28]([CH2:27][C@H:3]([OH:10])[CH2:4][N:2]2[C:3](=[O:10])[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:11])[CH2:30][CH2:5]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6809PhthalimideHCID 685803253,4-Dichlorophenoxypiperidine

Product 1

HCID 59295988(S)-2-[3-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-2-Oxiranylmethyl)-1H-isoindole-1,3-(2H)-dione (Tetrahedron Asymmetry, 1996, 7, 1641, 5 g) in a mixture of 50 ml of ethanol and 15 ml of DMF was treated with 4 (3,4-dichlorophenoxy)-piperidine (6 g). The mixture was stirred overnight at room temperature. The solution was concentrated under vacuum and the residue was azeotroped twice with toluene. The crude material was purified by chromatography (ethyl acetate) to give the subtitle compound as a yellow oil.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. customthe residue was azeotroped twice with toluene
  3. customThe crude material was purified by chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-500494ac285c46ea80ece8624a640640
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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