Triethylamine → HCID 59331961, compound

HRID 2361772Notes

Reaction equation

HRID 2361772 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>ClCCl.C(OCC)(=O)C>[CH2:32]([O:31][C:29]([N:11]1[CH2:12][CH2:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:9][CH2:10]1)=[O:30])[CH3:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 497607774-(4-Bromophenyl)-4-(4-chlorophenyl)piperidine

Product 1

HCID 59331961HCID 59331961, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring suspension of 4-(4-Bromo-phenyl)-4-(4-chloro-phenyl)-piperidine* (0.28 g, 0.80 mmol) in dichloromethane (10 ml), were added triethylamine (0.45 ml, 3.2 mmol) and ethyl chloroformate (0.085 ml, 0.88 mmol). The reaction mixture was stirred for 3 hours, diluted with ethyl acetate and washed with 1N HCl, saturated sodium hydrogen carbonate and brine. The organic layer was separated, dried (MgSO4), filtered and concentrated to afford the title compound (0.29 g, 94% yield). LCMS: (PS-A2), Rt 4.02 [M+H]+ 422, 424. *This starting material can be made by the method described in Example 14A

Workup

  1. washwashed with 1N HCl, saturated sodium hydrogen carbonate and brine
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3afd52c325d84128a31fb8e02c5507a2
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

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