Trifluoroacetic acid → Benzyl (3-methoxy-4-piperidin-4-ylphenyl)carbamate

HRID 869253Notes

Reaction equation

HRID 869253 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)=[C:14]([O:31][CH3:32])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCCl>[CH3:32][O:31][C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:17]=[CH:16][C:15]=1[CH:18]1[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66642793Tert-butyl 4-(4-{[(benzyloxy)carbonyl]amino}-2-methoxyphenyl)piperidine-1-carboxylate

Product 1

HCID 86662054Benzyl (3-methoxy-4-piperidin-4-ylphenyl)carbamateYield 85.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of tert-butyl 4-(4-{[(benzyloxy)carbonyl]amino}-2-methoxyphenyl)piperidine-1-carboxylate (Preparation Example 454) (4.92 g), trifluoroacetic acid (10 mL) and 1,2-dichloroethane (50 mL) was stirred at room temperature for 1 hour. The reaction solvent was concentrated under reduced pressure, and after addition of saturated aqueous sodium hydrogen carbonate, the residue was extracted with chloroform. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was solidified by addition of diethyl ether to give benzyl (3-methoxy-4-piperidin-4-ylphenyl)carbamate (3.24 g) as a white solid.

Workup

  1. concentrationThe reaction solvent was concentrated under reduced pressure
  2. additionafter addition of saturated aqueous sodium hydrogen carbonate
  3. extractionthe residue was extracted with chloroform
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. additionthe residue was solidified by addition of diethyl ether

Sources & evidence

ORD record
ord-2e0ed21dc2514555a4532f69df73fa75
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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