Butyl isocyanate → HCID 67421830, compound

HRID 880719Notes

Reaction equation

HRID 880719 reaction equation
[CH2:1]([N:5]=[C:6]=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:19]=[CH:18][C:17]=1[CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1.C(N(CC)C(C)C)(C)C>[CH2:1]([NH:5][C:6]([N:33]1[CH2:32][CH2:31][CH:30]([C:17]2[CH:18]=[CH:19][C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:21][C:16]=2[O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:35][CH2:34]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8110Butyl isocyanateHCID 67422789HCID 67422789, compound

Product 1

HCID 67421830HCID 67421830, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 81531DiisopropylethylamineSolvent

Procedure

In a 10 ml round-bottomed flask, 0.25 g of 4-(2,4-bis(benzyloxy)phenyl)piperidine is dissolved in 5 ml of tetrahydrofuran in the presence of 0.23 ml of N,N-diisopropylethylamine. 0.08 ml of butyl isocyanate is added and the reaction mixture is then stirred for 20 minutes at ambient temperature. The reaction mixture is extracted with ethyl acetate, and then the organic phases are combined and dried over magnesium sulphate. The residue is chromatographed on silica gel (8/2 heptanelethyl acetate). 0.25 g of 4-(2,4-bis(benzyloxy)phenyl)piperidine-1-carboxylic acid butylamide is obtained. Yield=78%.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. customThe residue is chromatographed on silica gel (8/2 heptanelethyl acetate)

Sources & evidence

ORD record
ord-622dead131414ca8b6d4152cb3ec4a02
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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