Diisopropylethylamine → 4-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine-1-carbonitrile

HRID 1622225Notes

Reaction equation

HRID 1622225 reaction equation
[CH2:1]([N:3](C(C)C)C(C)C)C.[CH3:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[O:27][CH:26]([CH:28]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[CH2:25][C:24]=3[CH:34]=2)=[CH:16][CH:15]=1)(=[O:13])=[O:12].Cl.C(N(C(C)C)C(C)C)C>ClCCl.O1CCCC1.O.C(OCC)(=O)C>[CH3:10][S:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[O:27][CH:26]([CH:28]4[CH2:33][CH2:32][N:31]([C:1]#[N:3])[CH2:30][CH2:29]4)[CH2:25][C:24]=3[CH:34]=2)=[CH:18][CH:19]=1)(=[O:12])=[O:13]

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 10997398Ethylbis(propan-2-yl)amine hydrochlorideHCID 679732894-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine

Product 1

HCID 866756724-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine-1-carbonitrile

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyldiisopropylamine (0.96 mL) and bromonitirile (175 mg) are added to a solution of 4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine (400 mg) in dichloromethane (10 mL) and tetrahydrofuran (10 mL), and the reaction mixture is stirred over night at room temperature. Dichloromethane and water are added and the organic phase is separated and washed with water, 10% NH4Cl solution, and brine, and dried over MgSO4. The solvent is evaporated and the residue is triturated with diethyl ether to give a brownish solid. Since this material still contains ethyldiisopropylamine hydrochloride, ethyl acetate and water are added. The organic phase is separated, dried over MgSO4 and concentrated in vacuo. The residue is again triturated with diethyl ether to afford the title compound. LC (method 2): tR=1.18 min; Mass spectrum (ESI+): m/z=383 [M+H]+.

Workup

  1. customthe organic phase is separated
  2. washwashed with water, 10% NH4Cl solution, and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent is evaporated
  5. customthe residue is triturated with diethyl ether
  6. customto give a brownish solid
  7. customThe organic phase is separated
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue is again triturated with diethyl ether

Sources & evidence

ORD record
ord-1c4b05e560cb4bbaa14df86876005651
Source dataset
uspto-grants-2014_07
Patent number
US08778926B2

Reaction notes

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