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Water → HCID 67421889, compound

HRID 2070070
Notes
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Reaction equation

HRID 2070070 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 103327734-Nitrophenyl pyridin-2-ylcarbamateHCID 67422788HCID 67422788, compound

Product 1

HCID 67421889HCID 67421889, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

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

  1. temperatureIt is heated at 80° C. for 24 hours
  2. extractionthe reaction mixture is then extracted with 50 ml of ethyl acetate
  3. customThe solvents are evaporated off
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes