Triethylamine → HCID 68582989, compound

HRID 2233378Notes

Reaction equation

HRID 2233378 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.[CH3:16][C@@:17]1([CH2:20][N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])[CH2:19][O:18]1.C(N(CC)CC)C>C(O)C.ClCCl>[NH3:9].[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]([CH2:19][C@:17]([OH:18])([CH3:16])[CH2:20][N:21]2[C:22](=[O:31])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]2=[O:30])[CH2:8][CH2:7]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 37320424-(3,4-Dichlorophenoxy)piperidineHCID 59296009HCID 59296009, compound

Product 2

HCID 222AmmoniaYield 2%HCID 68582989HCID 68582989, compoundYield 133.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3,4-dichlorophenoxy)piperidine (0.985 g, 4 mmoles), 2-[[(2R)-2-methyloxiranyl]methyl]-1H-isoindole-1,3(2H)-dione (0.869 g, 4 mmoles) and triethylamine (0.809 g, 1.12 ml, 8 mmoles) in ethanol (20 ml) was stirred at 50° C. for 5 h. The resulting solution was cooled to room temperature and concentrated in vacuo to leave a crude yellow gum. Flash chromatography (silica, 2% of 7N methanolic ammonia in dichloromethane as eluant) afforded the subtitle compound as a yellow oil (1.24 g).

Workup

  1. concentrationconcentrated in vacuo
  2. customto leave a crude yellow gum

Sources & evidence

ORD record
ord-7bdc3112a2e44a6dae4893219b0624cb
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

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