Water → HCID 178443563, compound

HRID 1198846Notes

Reaction equation

HRID 1198846 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[CH:2][CH3:3].C(N(CC)CC)C.[CH2:17]([C@H:24]1[CH2:29][CH2:28][C@H:27]([C:30](=[O:34])[CH:31]=[CH:32]Cl)[CH2:26][CH2:25]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].O>C(OCC)C>[CH2:17]([C@H:24]1[CH2:29][CH2:28][C@H:27]([C:30](=[O:34])[CH:31]=[CH:32][C:2]([CH3:3])=[CH:1][N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:26][CH2:25]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 138954N-(1-propenyl)piperidineHCID 178443564HCID 178443564, compound

Product 1

HCID 178443563HCID 178443563, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 6 g of N-(1-propenyl)piperidine, 45 ml of of diethyl ether and 4.36 ml of triethylamine is treated dropwise while stirring and gassing with nitrogen at 0° C. within 1 hour with a solution of 8.5 g of trans-4-heptyl-1-(3-chloroacryloyl)cyclohexane in 20 ml of diethyl ether. The suspension is stirred at 0° C. for a further 1 hour and then treated with 120 ml of water and extracted three times with diethyl ether. The organic phases are washed twice with water, dried over sodium sulphate, filtered and concentrated, there being obtained N-[5-(trans-4-heptylcyclohexyl)-2-methyl-5-oxo-1,3-pentadienyl]piperidine.

Workup

  1. additionis treated dropwise
  2. stirringThe suspension is stirred at 0° C. for a further 1 hour
  3. extractionextracted three times with diethyl ether
  4. washThe organic phases are washed twice with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a9dfba4aa674e97aea9d2912f9ab059
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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