Sodium Chloride → 1-[2-(3,5-Dimethoxyphenyl)ethyl]-alpha-(3,5-dimethoxyphenyl)-alpha-(1-methylethyl)-piperidine-3-propanenitrile

HRID 1979533Notes

Reaction equation

HRID 1979533 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH:14]([CH3:16])[CH3:15])[C:12]#[N:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH:31]([CH2:35]Cl)[CH2:30]2)[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1.[Na+].[Cl-]>C1COCC1>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH:31]([CH2:35][C:11]([C:5]3[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)([CH:14]([CH3:16])[CH3:15])[C:12]#[N:13])[CH2:30]2)[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 141836211-[2-(3,5-Dimethoxyphenyl)ethyl]-3-chloromethylpiperidineHCID 14183624alpha-Isopropyl-3,5-dimethoxyphenylacetonitrile

Product 1

HCID 141836511-[2-(3,5-Dimethoxyphenyl)ethyl]-alpha-(3,5-dimethoxyphenyl)-alpha-(1-methylethyl)-piperidine-3-propanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

The reaction mixture is stirred at -50° C. for 20 minutes, a solution of 2.75 g (0.0125 mol) of the nitrile prepared under (a) in 10 cc of THF is then added dropwise, the mixture is stirred again at -50° C. for 30 minutes and a solution of 3 g of the compound prepared under (b) in 10 cc of THF is then added. The reaction mixture is stirred for 1 hour at -50° C. and then left to stand overnight at ambient temperature. It is poured into 0.5 liter of a water/ice mixture, saturated with NaCl and extracted with diethyl ether. The organic phase is dried and evaporated. The oil obtained is chromatographed on a silica 60 column, elution being carried out with a 70/30 CH2Cl2 /acetone mixture.

Workup

  1. additionis then added dropwise
  2. stirringthe mixture is stirred again at -50° C. for 30 minutes
  3. additionis then added
  4. stirringThe reaction mixture is stirred for 1 hour at -50° C.
  5. waitleft
  6. waitto stand overnight at ambient temperature
  7. extractionextracted with diethyl ether
  8. customThe organic phase is dried
  9. customevaporated
  10. customThe oil obtained
  11. customis chromatographed on a silica 60 column, elution

Sources & evidence

ORD record
ord-c295a7730fa74cc1a4680abb0f1533a9
Source dataset
uspto-grants-1984_11
Patent number
US04481207

Reaction notes

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