2,6-Xylyl isocyanate → HCID 18456131, compound

HRID 1271918Notes

Reaction equation

HRID 1271918 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([OH:20])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:4][CH2:3]1.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1[N:29]=[C:30]=[O:31]>ClCCl>[CH3:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([CH3:21])[C:23]=1[NH:29][C:30]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([OH:20])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:4][CH2:3]1)=[O:31]

Participants

4

Reactant 2

HCID 987872,6-Xylyl isocyanate2×HCID 21935532HCID 21935532, compound

Product 1

HCID 18456131HCID 18456131, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-aminopiperidyl)-3-(2-methoxyphenoxy)propan-2-ol (40 mg) and 2,6-dimethylphenylisocyanate (30 μl) in dichloromethane (1 ml) was refluxed for 2 hours, after which time a further 20 μl of 2,6-dimethylphenylisocyanate was added, and the mixture refluxed for a further 2 hours. Solvent was removed under reduced pressure, and the residue flash chromatographed (0–6% methanol/dichloromethane), to provide [(2,6-dimethylphenyl)amino]-N-{1-[2-hydroxy-3-(2-methoxyphenoxy)propyl](4-piperidyl)}carboxamide.

Workup

  1. temperaturethe mixture refluxed for a further 2 hours
  2. customSolvent was removed under reduced pressure
  3. customthe residue flash chromatographed (0–6% methanol/dichloromethane)

Sources & evidence

ORD record
ord-d4919ffbfbf242caabd6041f1ea3606a
Source dataset
uspto-grants-2007_04
Patent number
US07208496B2

Reaction notes

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