Butyl isocyanate → HCID 67421830, compound

HRID 2365914Notes

Reaction equation

HRID 2365914 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 heptane/ethyl 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 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-7bfa1329f0584f2e8c5b206e58e57f85
Source dataset
uspto-grants-2014_04
Patent number
US08697726B2

Reaction notes

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