Water → (4-Aminophenyl)(piperidin-1-yl)methanone

HRID 902184Notes

Reaction equation

HRID 902184 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.O>C(Cl)Cl.CCN(CC)CC>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9784-Aminobenzoic AcidHCID 8082PiperidineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

Product 1

HCID 577812(4-Aminophenyl)(piperidin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 100 mg 4-Amino-benzoic acid in 1 mL DCM and 0.2 mL NEt3, 62 mg piperidine and 184 mg BOP-Cl were added at RT and the mixture was stirred for 16 h. After the addition of 5 mL water the mixture was filtered through a chem elut® cartridge by elution with ethyl acetate and then concentrated under reduced pressure. The residue was directly subjected to the subsequent amide coupling reaction without further purification. Yield: 125 mg.

Workup

  1. filtrationwas filtered through a chem elut® cartridge by elution with ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was directly subjected to the subsequent amide coupling reaction without further purification

Sources & evidence

ORD record
ord-4c8a68deb0b14b04851e41e965c3df60
Source dataset
uspto-grants-2008_04
Patent number
US07365088B2

Reaction notes

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