Benzoyl chloride → HCID 68527259, compound

HRID 884159Notes

Reaction equation

HRID 884159 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[C:5]([NH:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)=[O:6].C(N(CC)CC)C.[C:39](Cl)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[Cl:31])[C:5]([NH:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][C:13]2[CH:14]=[CH:15][C:16]([N:19]3[CH2:20][CH2:21][CH:22]([O:25][C:39](=[O:46])[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:23][CH2:24]3)=[CH:17][CH:18]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 68526975HCID 68526975, compound

Product 1

HCID 68527259HCID 68527259, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{4-[4-(3,4-dichlorobenzoylamino)phenoxy]phenyl}-4-hydroxypiperidine (200 mg, 0.44 mmol) in dichloromethane (8 mL) were added with triethylamine (0.091 mL, 0.65 mmol), benzoyl chloride (74 mg, 0.53 mmol) and 4-(dimethylamino)pyridine (3 mg, 0.025 mmol), and the resulting solution was stirred for 2.5 days at room temperature. This reaction solution was purified by silica gel column chromatography (methanol:dichloromethane=7:93), to thereby yield 80 mg of the title compound.

Workup

  1. customThis reaction solution was purified by silica gel column chromatography (methanol:dichloromethane=7:93)

Sources & evidence

ORD record
ord-d17f436706cc43e6a70751dca87f8069
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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