Water → HCID 67421889, compound

HRID 2070070Notes

Reaction equation

[Cl-].[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][C:11]=1[CH:24]1[CH2:29][CH2:28][NH2+:27][CH2:26][CH2:25]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[N+](C1C=CC([O:48][C:49](=O)[NH:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][N:52]=2)=CC=1)([O-])=O.O>CN(C)C=O>[N:52]1[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=1[NH:50][C:49]([N:27]1[CH2:28][CH2:29][CH:24]([C:11]2[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:15][C:10]=2[O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:25][CH2:26]1)=[O:48]

Participants

Conditions

Temperature: 80 °C

Procedure

0.5 g of 4-(2,4-bis(benzyloxy)phenyl)piperidinium chloride is suspended in 5 ml of dimethylformamide and then 0.43 ml of N,N-diisopropylethylamine is added, as is 0.38 g of pyridin-2-ylcarbamic acid 4-nitrophenyl ester in solution in 2 ml of dimethylformamide. The reaction mixture is stirred for 24 hours at 80° C. It is heated at 80° C. for 24 hours. 50 ml of water are added, and the reaction mixture is then extracted with 50 ml of ethyl acetate. The solvents are evaporated off and then the residue is chromatographed on silica gel (70/30 heptane/ethyl acetate). 20 mg of 4-(2,4-bis(benzyloxy)phenyl)piperidine-1-carboxylic acid pyridin-2-ylamide are obtained.

Workup

temperatureIt is heated at 80° C. for 24 hours
extractionthe reaction mixture is then extracted with 50 ml of ethyl acetate
customThe solvents are evaporated off
customthe residue is chromatographed on silica gel (70/30 heptane/ethyl acetate)

Sources & evidence

ORD record: ord-499a970afbee4185ab791204608588a3
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299259B2

Reaction notes

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