3-Anilinopropionitrile → HCID 70571742, compound

HRID 441318Notes

Reaction equation

HRID 441318 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([N:22]([CH3:24])[CH3:23])[C:15]=1[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:6](O)CS(C)(=O)=O.C[O-].[Na+].[NH:29]([CH2:36][CH2:37][C:38]#[N:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CS(C)=O>[NH:29]([CH:36]=[C:37]([CH2:6][C:5]1[CH:13]=[C:14]([N:22]([CH3:23])[CH3:24])[C:15]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)=[C:3]([N:2]([CH3:1])[CH3:25])[CH:4]=1)[C:38]#[N:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 54062804HCID 54062804, compound

Product 1

HCID 70571742HCID 70571742, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 7.4 g. of 3,5-bis(dimethylamino)-α-[(methylsulfonyl)methyl]-4-piperidinobenzyl alcohol, 1.64 g. of sodium methylate and 4.4 g. of β-anilinopropionitrile in 40 ml. of dimethylsulfoxide was stirred for 2 hours at 50° C. under nitrogen. The mixture was poured into 250 ml. of water, the precipitated product extracted with ethyl acetate, the ethyl acetate solution dried over sodium sulfate and evaporated. By purification of the residue over aluminum oxide with benzene and recrystallization from ethyl acetate/petroleum ether, there was obtained α-(anilinomethylene)-3,5-bis(dimethylamino)-4-piperidinohydrocinnamonitrile having a melting point of 200°-202° C.

Workup

  1. additionA mixture of 7.4 g
  2. additionThe mixture was poured into 250 ml
  3. extractionof water, the precipitated product extracted with ethyl acetate
  4. dry with materialthe ethyl acetate solution dried over sodium sulfate
  5. customevaporated
  6. customBy purification of the residue over aluminum oxide
  7. customwith benzene and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-0daa367864f5423cbfd98fbeb50e4127
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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