O-Phenylenediamine → HCID 67357285, compound

HRID 1879352Notes

Reaction equation

HRID 1879352 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17](=[O:19])[NH:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH2:27])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidHCID 2724699PyBOP

Product 1

HCID 67357285HCID 67357285, compoundYield 212.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.5 g of piperidine-1,4-dicarboxylic acid monobenzyl ester, 1.5 g of phenylendiamine, 2.3 mL of DIPEA and 6.9 g of PyBOP in 40 mL of DCM was stirred overnight at rt. The reaction was quenched with H2O, extracted with DCM, dried over MgSO4 and concentrated in vacuo to obtain 10 g of the desired compound as crude brown solid.

Workup

  1. customThe reaction was quenched with H2O
  2. extractionextracted with DCM
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57c69664e00e4c62a05000d082066936
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Reaction notes

Loading…