Triethylamine → HCID 59331961, compound

HRID 924707Notes

Reaction equation

HRID 924707 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-ca70acc1d13a41e5a33d1f6a40503d52
Source dataset
uspto-grants-2016_03
Patent number
US09283226B2

Reaction notes

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