Iodoethane → HCID 178464763, compound

HRID 2209800Notes

Reaction equation

HRID 2209800 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:25](I)[CH3:26]>CN(C)C=O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]([C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:13][CH2:14]2)[CH2:25][CH3:26])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178523575HCID 178523575, compound

Product 1

HCID 178464763HCID 178464763, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of trans-N-(4-chlorobenzoyl)-4-phenylcyclohexylamine in 20 ml of dimethylformamide are mixed with 0.14 g of 55% sodium hydride and after 15 minutes 0.62 g of ethyliodide are added. After 1 hour at ambient temperature the reaction solution is evaporated down, the residue is taken up in water, extracted with ethyl acetate and the organic phase is dried and evaporated down. After purification by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1 to 3:1, v:v), 0.73 g of the title compound are obtained, melting point 127°-129° C.

Workup

  1. additionare added
  2. customAfter 1 hour at ambient temperature the reaction solution is evaporated down
  3. extractionextracted with ethyl acetate
  4. customthe organic phase is dried
  5. customevaporated down
  6. customAfter purification by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1 to 3:1, v:v), 0.73 g of the title compound
  7. customare obtained

Sources & evidence

ORD record
ord-8aa78f5e2d2a4121a44fae65468d0e4d
Source dataset
uspto-grants-1995_10
Patent number
US05455273

Reaction notes

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