1,1'-Carbonyldiimidazole → HCID 86619596, compound

HRID 2236840Notes

Reaction equation

HRID 2236840 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:37][NH:38][O:39][CH3:40]>ClCCl>[CH3:40][O:39][N:38]([CH3:37])[C:21]([CH:18]1[CH2:17][CH2:16][N:15]([C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[CH:14][CH:13]=2)[CH2:20][CH2:19]1)=[O:23]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 68697801HCID 68697801, compound

Product 1

HCID 86619596HCID 86619596, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-{4-[(tert-butoxycarbonyl)amino]phenyl}piperidine-4-carboxylic acid (1.3 g, 4.1 mmol) in dichloromethane (40 mL) is added carbonyldiimidazole (0.79 g, 4.9 mmol) and the mixture is stirred at room temperature for 30 minutes before N,O-dimethylhydroxylamine hydrochloride (1.0 g, 10 mmol) is added. After stirring for 30 minutes, the reaction mixture is concentrated under reduced pressure. The residue is partitioned between diethyl ether and water. The ethereal phase is washed 2× with water and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide tert-butyl [4-(4-{[methoxy(methyl)amino]carbonyl}piperidin-1-yl)phenyl]carbamate as a pale yellow solid (1.5 g, 100%).

Workup

  1. additionis added
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. customThe residue is partitioned between diethyl ether and water
  4. washThe ethereal phase is washed 2× with water
  5. dry with materialonce with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2248b758266b4e30be9966351c4388a2
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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