Water → HCID 20537467, compound

HRID 1155690Notes

Reaction equation

HRID 1155690 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7](Br)[CH:8]=[CH2:9].Cl.[NH:12]1[C:20]2[C:15](=[C:16]([C:21]3([OH:27])[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]3)[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:7]([N:23]1[CH2:24][CH2:25][CH2:26][C:21]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:15]=2[CH:14]=[CH:13][NH:12]3)([OH:27])[CH2:22]1)[CH:8]=[CH2:9]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 12900686HCID 12900686, compound

Product 1

HCID 20537467HCID 20537467, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

22.9 g of sodium carbonate and 7.6 ml of allyl bromide were added to a mixture of 18 g of 3-(1H-indol-4-yl)-3-piperidinol hydrochloride in 350 ml of dimethylformamide and the mixture was stirred under an inert atmosphere at room temperature for 2 hours. Then, one liter of water and 500 ml of ethyl acetate were added thereto and the decanted organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The 17 g of residue were chromatographed over silica gel and eluted with a 6-3-1 cyclohexanechloroform-triethylamine mixture to obtain 14 g of 1-(2-propenyl)-3-(1H-indol-4-yl)-3-piperidinol with an Rf=0.15.

Workup

  1. washthe decanted organic phase was washed with water
  2. customdried
  3. customevaporated to dryness under reduced pressure
  4. customThe 17 g of residue were chromatographed over silica gel
  5. washeluted with a 6-3-1 cyclohexanechloroform-triethylamine mixture

Sources & evidence

ORD record
ord-6651c45bc9224a1e81991c7b1f4e7489
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

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