Cycloheptylamine → HCID 22163931, compound

HRID 1087789Notes

Reaction equation

HRID 1087789 reaction equation
[CH:1]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O:10][CH:11]1[CH:15]([CH:16]=O)[CH2:14][CH:13](OC)O1>C(O)(=O)C>[CH:1]1([N:8]2[CH:13]=[CH:14][C:15]([CH:11]=[O:10])=[CH:16]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2899CycloheptylamineHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde

Product 1

HCID 22163931HCID 22163931, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 38.0 g of cycloheptylamine and 50 ml of 2,5-dimethoxytetrahydrofuran-3-carboxaldehyde in 300 ml of glacial acetic acid is stirred under reflux for 3 hours. The solution is evaporated to dryness at 60° under reduced pressure. The residue is then dissolved in a 1:1 mixture of ether and hexane, the solution is treated with charcoal and evaporated to dryness to give 1-cycloheptyl-1H-pyrrole-3-carboxaldehyde as an oil. The aldehyde (30 g) is then added dropwise to a mixture of 35 ml of triethyl phosphonoacetate in 1 liter of toluene to which had been added 9.5 g of sodium hydride. The reaction mixture is stirred in an ice bath for 2 hours and then at room temperature overnight, washed first with ice cold dilute hydrochloric acid, then with brine, dried over magnesium sulfate, treated with charcoal and evaporated to dryness to yield ethyl (E)-3-(1-cycloheptyl-1H-pyrrol-3-yl)-2-propenoate.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe solution is evaporated to dryness at 60° under reduced pressure
  3. dissolutionThe residue is then dissolved in a 1:1 mixture of ether and hexane
  4. additionthe solution is treated with charcoal
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-31bee25633df46ca8b6553fb2e92d421
Source dataset
uspto-grants-1990_10
Patent number
US04960787

Reaction notes

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