Triethylamine → HCID 57496385, compound

HRID 537738Notes

Reaction equation

HRID 537738 reaction equation
[CH:1]1([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][CH2:9][NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([CH:7]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][CH2:9][N:8]2[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 574963842-Cyclohexyl-4-phenylpiperidine

Product 1

HCID 57496385HCID 57496385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-cyclohexyl-4-phenylpiperidine (2.85 g, 11.71 mmol) in CH2Cl2 (58.5 ml) was added benzyl chloroformate (2.507 ml, 17.56 mmol) and triethylamine (2.45 ml, 17.56 mmol). The reaction was stirred at room temperature for 2 hours. Added water and extracted 3 times with CH2Cl2. The combined organics were dried, concentrated, and purified on silica gel 20% EtOAc/Hexanes. Separated cis and trans on the AD column, 20% IPA/Hexanes w/DEA. Peak 1 corresponds to the cis racemic mixture with one trans diastereomer and peak2 is a single trans diastereomer. Obtained 2.5 g racemic cis/trans peak1. Resolved on the OJ column 20% EtOH/Hexanes w/DEA: Peak 1: 0.68 g pure cis undesired, peak 2 1.75 g cis/trans mixture.

Workup

  1. extractionAdded water and extracted 3 times with CH2Cl2
  2. customThe combined organics were dried
  3. concentrationconcentrated
  4. custompurified on silica gel 20% EtOAc/Hexanes
  5. customSeparated cis and trans on the AD column, 20% IPA/Hexanes
  6. customObtained 2.5 g racemic cis/trans peak1

Sources & evidence

ORD record
ord-0bd2339d22c942ef9167d6aff07e2e7b
Source dataset
uspto-grants-2014_10
Patent number
US08865701B2

Reaction notes

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