2,6-Lutidine → HCID 59252700, compound

HRID 388537Notes

Reaction equation

HRID 388537 reaction equation
[CH2:1](N1CCC(NC2C=CC=C(F)C=2)(C#N)CC1)[C:2]1C=CC=CC=1.C(C(C(Cl)=O)C(Cl)=O)C.N1C(C)=CC=CC=1C.[CH2:41]([N:48]1[CH2:53][CH2:52][C:51]([N:56]([C:63]2[CH:68]=[CH:67][CH:66]=[C:65]([F:69])[CH:64]=2)[C:57](=[O:62])[CH2:58][C:59]([OH:61])=[O:60])([C:54]#[N:55])[CH2:50][CH2:49]1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl>[CH2:41]([N:48]1[CH2:53][CH2:52][C:51]([N:56]([C:63]2[CH:68]=[CH:67][CH:66]=[C:65]([F:69])[CH:64]=2)[C:57](=[O:62])[CH2:58][C:59]([O:61][CH2:1][CH3:2])=[O:60])([C:54]#[N:55])[CH2:50][CH2:49]1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 109209242-Ethylpropanedioyl dichloride2×HCID 46938834HCID 46938834, compoundHCID 86640244HCID 86640244, compound

Product 1

HCID 59252700HCID 59252700, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-benzyl-4-[(3-fluorophenyl)amino]piperidine-4-carbonitrile (Intermediate 1A.1-1, 9.0 g, 29.1 mmol) in dichloromethane (150 ml) were added ethyl malonyl chloride (4.9 ml, 37.8 mmol) and 2,6-lutidine (5.1 ml, 43.6 mmol). The reaction was allowed to stir at rt for 2.5 h. Additional ethyl malonyl chloride (1.1 ml, 8.7 mmol) was added, and the reaction was allowed to stir for 30 min. The reaction was diluted with dichloromethane and washed with water and brine. The organic portion was dried over sodium sulfate, filtered, and concentrated in vacuo to yield a 1:1 mixture of desired ester ethyl 3-[(1-benzyl-4-cyanopiperidin-4-yl)(3-fluorophenyl)amino]-3-oxopropanoate and its acid 3-[(1-benzyl-4-cyanopiperidin-4-yl)(3-fluorophenyl)amino]-3-oxopropanoic acid (quant).

Workup

  1. stirringto stir for 30 min
  2. washwashed with water and brine
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield

Sources & evidence

ORD record
ord-4dbc39938e6f4290a9976cf1d4bc9c99
Source dataset
uspto-grants-2013_02
Patent number
US08377954B2

Reaction notes

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