Benzoylacetonitrile → HCID 68868816, compound

HRID 1784361Notes

Reaction equation

HRID 1784361 reaction equation
S(O)(C1C=CC(C)=CC=1)(=O)=O.O.[C:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O=[C:27]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:28][C:29]#[N:30]>C1C=CC=CC=1>[C:29]([CH:28]=[C:27]([N:23]1[CH2:22][CH2:21][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:25][CH2:24]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)#[N:30]

Participants

5

Reactant 3

HCID 64799BenzoylacetonitrileHCID 143452tert-Butyl piperazine-1-carboxylateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 68868816HCID 68868816, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
115 °C

Procedure

TsOH—H2O (1 g) was added into a solution of N-Boc piperazine (50 g) and 3-oxo-3-phenylpropanenitrile (19.49 g) in benzene (200 ml). The reaction mixture was heated up to 115° C. for 16 hours and resultant water was collected by Dean-Stark trap. After the solution was concentrated, a residue was obtained and further purification using silica gel chromatography provided tert-butyl 4-(2-cyano-1-phenylvinyl)piperazine-1-carboxylate. 1H NMR (500 MHz, CD3OD) δ7.91 (m, 5H), 5.24 (s, 1H), 3.89-3.50 (m, 8H), 1.88 (s, 9H); 13C NMR (125 MHz, CD3OD) δ167.6, 155.7, 135.4, 130.6, 129.4, 121.8, 81.1, 67.1, 45.4, 28.0. MS m/z: (M+H)+ calcd for C18H24N3O2 314.19, found 314.25. Retention time 1.81 min (column D).

Workup

  1. customresultant water was collected by Dean-Stark trap
  2. concentrationAfter the solution was concentrated
  3. customa residue was obtained
  4. customfurther purification

Sources & evidence

ORD record
ord-cdffe3ca95c74105ab1185ec0bc6e856
Source dataset
uspto-grants-2009_03
Patent number
US07504399B2

Reaction notes

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