Dimethylformamide → HCID 68829666, compound

HRID 747724Notes

Reaction equation

HRID 747724 reaction equation
Cl[CH2:2][C@@H:3]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:4][C:5]1[CH:27]=[CH:26][C:8]([O:9][CH:10]2[CH2:15][CH2:14]CN(C(OCC3C=CC=CC=3)=O)[CH2:11]2)=[CH:7][CH:6]=1.[C:36]([C:38]1[CH:39]=[C:40]([OH:44])[CH:41]=[CH:42][CH:43]=1)#[N:37].C(=O)([O-])[O-].[K+].[K+].[C:51]([O:54][CH2:55][CH3:56])(=[O:53])C.C[N:58]([CH3:61])C=O>>[CH2:55]([O:54][C:51]([N:58]1[CH2:61][CH2:11][CH:10]([O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C@H:3]([NH:28][C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH2:2][O:44][C:40]3[CH:39]=[C:38]([CH:43]=[CH:42][CH:41]=3)[C:36]#[N:37])=[CH:27][CH:26]=2)[CH2:15][CH2:14]1)=[O:53])[C:56]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 68831136HCID 68831136, compound

Product 1

HCID 68829666HCID 68829666, compound

Conditions

Temperature
70 °C

Procedure

6.4 g (12.7 mmol) of benzyl 3-[4-[(2S)-3-chloro-2-(t-butoxycarbonylamino)propyl]phenoxy]piperidine-1-carboxylate was dissolved in 70 ml of dimethylformamide. 2.27 g (19.1 mmol) of 3-cyanophenol and 3.51 g (25.4 mmol) of potassium carbonate were added to the solution, and they were stirred at 70° C. for 15 hours. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-41993a7b49324dfd83f34327f68783b6
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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