Acetic Anhydride → HCID 15392198, compound

HRID 362501Notes

Reaction equation

HRID 362501 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:34]=[CH:33][C:18]([NH:19][CH2:20][C:21]3[CH:30]=[C:29]4[C:24]([CH:25]=[CH:26][C:27]([C:31]#[N:32])=[CH:28]4)=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:35](OC(=O)C)(=[O:37])[CH3:36].C(OCC)(=O)C>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N:19]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]4[C:29](=[CH:28][C:27]([C:31]#[N:32])=[CH:26][CH:25]=4)[CH:30]=3)[C:35](=[O:37])[CH3:36])=[CH:33][CH:34]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 15392197HCID 15392197, compound

Product 1

HCID 15392198HCID 15392198, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

7-[[4-[(1-t-Butoxycarbonyl-4-piperidyl)oxy]anilino]methyl]-2-naphthalenecarbonitrile obtained in Reference Example 2 (150 mg) was dissolved in 1 ml of pyridine, 268 mg of acetic anhydride and 10 mg of 4-dimethylaminopyridine were added to the solution, and the mixture was stirred at room temperature for 15 hours. Ethyl acetate was added to the reaction solution. The mixture was washed with 10% citric acid aqueous solution and saturated sodium bicarbonate aqueous solution in that order, dried over anhydrous sodium sulfate, and then evaporated. By recrystallizing the resulting residue from ethanol, 139 mg of N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-N-[(7-cyano-2-naphthyl)methyl]acetamide was obtained.

Workup

  1. washThe mixture was washed with 10% citric acid aqueous solution and saturated sodium bicarbonate aqueous solution in that order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated
  4. customBy recrystallizing the resulting residue from ethanol

Sources & evidence

ORD record
ord-d6f4cdf007de48ccac9723a753329e3a
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

Loading…