5-Isocyanato-1,2,3-trimethoxybenzene → HCID 10098735, compound

HRID 1251332Notes

Reaction equation

HRID 1251332 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:13]=[C:14]=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Cl:16][C:17]1[CH:18]=[C:19]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH2:27][C@H:28]([NH2:32])[CH:29]([CH3:31])[CH3:30])[CH2:23][CH2:22]1>C(Cl)Cl>[Cl:16][C:17]1[CH:18]=[C:19]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:20][CH:21]1[CH2:22][CH2:23][N:24]([CH2:27][C@H:28]([NH:32][C:14]([NH:13][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)=[O:15])[CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 5177665-Isocyanato-1,2,3-trimethoxybenzeneHCID 22943538HCID 22943538, compound

Product 1

HCID 10098735HCID 10098735, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,4,5-Trimethoxyphenyl isocyanate (1.9 g, 9.11 mmol) was added to a solution of 1-(R)-[4-(3,4-dichlorobenzyl)piperidin-1-ylmethyl]-2-methylpropylamine (2.5 g, 7.59 mmol) in methylene chloride (25 ml) under argon atmosphere. The solution was stirred for 45 min., at room temperature, followed by 30 min., at 38° C. The reaction mixture was concentrated in vacuo. The crude product was chromatographed on a silica gel column, eluting with 1.5-2.5% MeOH/CH2Cl2 containing 1% NH4OH to give 1-{1-(R)-[4-(3,4-dichlorobenzyl)piperidin-1-ylmethyl]-2-methylpropyl}-3-(3,4,5-trimethoxyphenyl)urea (3.7 g).

Workup

  1. waitfollowed by 30 min., at 38° C
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe crude product was chromatographed on a silica gel column
  4. washeluting with 1.5-2.5% MeOH/CH2Cl2 containing 1% NH4OH

Sources & evidence

ORD record
ord-5e968fb906904ce88d3fb5bf0ef13c75
Source dataset
uspto-grants-2002_01
Patent number
US06342509B1

Reaction notes

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