Triethylamine → HCID 118037313, compound

HRID 715557Notes

Reaction equation

HRID 715557 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([NH:14][C:23](=[O:24])[O:25][CH2:26][CH3:27])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 57365150HCID 57365150, compound

Product 1

HCID 118037313HCID 118037313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Bromophenyl)piperidin-4-amine (255 mg) and triethylamine (280 μL) are dissolved in dichloromethane (3 mL), treated with ethyl chloroformate (105 μL) and stirred for 2 hours. The mixture is partitioned between dichloromethane and water. The organic phase is washed with water and the combined aqueous phases are extracted with dichloromethane. The organic phases are combined, washed with brine and dried (MgSO4). The solvents are evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:50) to give the title compound. LC (method 2): tR=1.04 min; Mass spectrum (ESI+): m/z=327 [M+H]+.

Workup

  1. customThe mixture is partitioned between dichloromethane and water
  2. washThe organic phase is washed with water
  3. extractionthe combined aqueous phases are extracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvents are evaporated
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:50)

Sources & evidence

ORD record
ord-e37e0927e97c4c6db41ad979f70df5e8
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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