1,1'-Carbonyldiimidazole → HCID 68504347, compound

HRID 1176263Notes

Reaction equation

HRID 1176263 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:46]=[CH:45][CH:44]=[CH:43][C:5]=1[O:6][CH2:7][CH2:8][O:9][CH:10]1[CH:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[CH:18][CH:17]=2)[CH2:14][CH2:13][N:12]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:11]1.[N:47]1([C:52](N2C=CN=C2)=[O:53])[CH:51]=[CH:50][N:49]=[CH:48]1>C(#N)C.COC(C)(C)C>[N:47]1([C:52]([O:1][CH2:2][CH2:3][C:4]2[CH:46]=[CH:45][CH:44]=[CH:43][C:5]=2[O:6][CH2:7][CH2:8][O:9][CH:10]2[CH:15]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])=[CH:20][CH:21]=3)[CH2:14][CH2:13][N:12]([C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])[CH2:11]2)=[O:53])[CH:51]=[CH:50][N:49]=[CH:48]1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 68505010HCID 68505010, compound

Product 1

HCID 68504347HCID 68504347, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 0.100 g of tert-butyl 3-{2-[2-(2-hydroxyethyl)phenoxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate (Example 26c) and 0.049 g of diimidazol-1-ylmethanone in 4 ml of acetonitrile is stirred at reflux over 5 hours. The reaction mixture is cooled at room temperature, diluted with tert-butyl methyl ether, washed with 1N HCl and 0.5N NaOH, dried over sodium sulphate and concentrated by evaporation. The crude title compound is obtained as a yellow oil from the residue. Rf=0.41 (2:1 EtOAc-heptane); Rt=5.61.

Workup

  1. temperatureat reflux over 5 hours
  2. washwashed with 1N HCl and 0.5N NaOH
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-dacedfd3624041adba059d94f1073434
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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