Triethylamine → HCID 86616768, compound

HRID 1784359Notes

Reaction equation

HRID 1784359 reaction equation
C(N(CC)CC)C.[C:8]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl[C:22]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[C:23]([C:26]#[N:27])[C:24]#[N:25]>CCO>[C:26]([C:23]([C:24]#[N:25])=[C:22]([N:18]1[CH2:17][CH2:16][N:15]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:20][CH2:19]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)#[N:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 176977alpha-Chlorobenzylidenemalononitrile

Product 1

HCID 86616768HCID 86616768, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethyl amine (1 ml) was added into a solution of N-Boc piperazine (1 g) and 2-(chloro(phenyl)methylene)malononitrile (1 g) in EtOH (20 ml). After 16 hours at 115° C., the reaction mixture was cooled down and some of desired product, tert-butyl 4-(2,2-dicyano-1-phenylvinyl)piperazine-1-carboxylate, precipitated out from the solution. After filteration, the mother solution was concentrated to offer a residue which was purified using silica gel chromatography to afford more tert-butyl 4-(2,2-dicyano-1-phenylvinyl)piperazine-1-carboxylate. 1H NMR (500 MHz, DMSO-d6) □7.53 (m, 5H), 3.93 (b, 2H), 3.61 (b, 2H), 3.36 (b, 2H), 3.15 (b, 2H), 1.39(s, 9H); 13C NMR(125 MHz, DMSO-d6) □170.9, 153.6, 132.6, 131.7, 129.1, 129.0, 117.4, 116.7, 79.4, 51.5, 50.33, 42.9, 27.9. MS m/z: (M+H)+ calcd for C19H23N4O2 339.18, found 339.17. Retention time 1.46 min (column A).

Workup

  1. temperaturethe reaction mixture was cooled down
  2. customsome of desired product, tert-butyl 4-(2,2-dicyano-1-phenylvinyl)piperazine-1-carboxylate, precipitated out from the solution
  3. concentrationAfter filteration, the mother solution was concentrated
  4. customwas purified

Sources & evidence

ORD record
ord-fa884b7c18a74d53a08928ef34d5e0f1
Source dataset
uspto-grants-2009_03
Patent number
US07504399B2

Reaction notes

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