Acetic Anhydride → HCID 68706126, compound

HRID 645486Notes

Reaction equation

HRID 645486 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:22](OC(=O)C)(=[O:24])[CH3:23].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:14][CH2:13][N:12]([C:22](=[O:24])[CH3:23])[CH2:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 49760176tert-Butyl [(4-phenylpiperidin-4-yl)methyl]carbamate

Product 1

HCID 68706126HCID 68706126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-phenylpiperidin-4-ylmethyl) carbamic acid tert-butyl ester (2.1 mmol) in CH2Cl2 is added acetic anhydride (3.1 mmol) and triethylamine (3.1 mmol) at 0° C. The reaction mixture is stirred at room temperature for 2.5 h then the bulk of solvent is concentrated in vacuo. After the residue is suspended in AcOEt, the mixture is washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo to give (1-acetyl-4-phenylpiperidin-4-ylmethyl)carbamic acid tert-butyl ester, which is directly used for the next reaction without further purification.

Workup

  1. concentrationthe bulk of solvent is concentrated in vacuo
  2. washthe mixture is washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-026b8dbfbef745ff9c3e7b97d39f684b
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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