Diisopropylethylamine → HCID 70895744, compound

HRID 1754912Notes

Reaction equation

HRID 1754912 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:45]([O:49][C:50]([N:52]1[CH2:57][CH2:56][C:55]([NH2:60])([C:58]#[N:59])[CH2:54][CH2:53]1)=[O:51])([CH3:48])([CH3:47])[CH3:46]>CN(C=O)C.O>[C:45]([O:49][C:50]([N:52]1[CH2:53][CH2:54][C:55]([C:58]#[N:59])([NH:60][C:10](=[O:12])[CH2:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH2:56][CH2:57]1)=[O:51])([CH3:48])([CH3:46])[CH3:47]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 882092,4-Dichlorophenylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22091429tert-Butyl 4-amino-4-cyanopiperidine-1-carboxylate

Product 1

HCID 70895744HCID 70895744, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2,4-Dichloro-phenyl)-acetic acid (218 mg, 1.07 mmol), 1-ethyl-3-(3′-dimethylamino-propyl)carbodiimide hydrochloride (255 mg, 1.33 mmol), 1-hydroxybenzotriazole hydrate (136 mg, 0.88 mmol) and N,N-diisopropylethylamine (0.378 ml, 2.22 mmol) were sequentially added to a solution of 4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 0.888 mmol) in DMF (4 ml) at room temperature, and the mixture was stirred at room temperature for 16 hours. H2O (20 ml) was added to the reaction mixture, followed by extraction with AcOEt (40 ml and 20 ml). The organic layers were sequentially washed with H2O (20 ml), 1 N HCl (20 ml), H2O (20 ml) and saturated brine (20 ml), and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt) to give 4-cyano-4-[2-(2,4-dichloro-phenyl)-acetylamino]-piperidine-1-carboxylic acid tert-butyl ester as a white powder (285 mg, 78%).

Workup

  1. extractionfollowed by extraction with AcOEt (40 ml and 20 ml)
  2. washThe organic layers were sequentially washed with H2O (20 ml), 1 N HCl (20 ml), H2O (20 ml) and saturated brine (20 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt)

Sources & evidence

ORD record
ord-14c41fbeead34de5b75c6fb643789cd1
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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