Dimethylformamide → HCID 13645768, compound

HRID 1982203Notes

Reaction equation

HRID 1982203 reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].[C:6]1([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[C:18]#[N:19])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:20]1COC[CH2:21]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:20][CH2:21][C:13]1([C:18]#[N:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8028Tetrahydrofuran2×HCID 13645775HCID 13645775, compound

Product 1

HCID 13645768HCID 13645768, compound

Procedure

In a 500 ml flask was added 0.88 g of freshly washed (with hexane) KH (2.2 eq, 22 mmoles). To this was added 100 ml THF, 50 ml DMF, and 10 mmoles of 2-phenylcyclohexane carbonitrile and the contents were heated at reflux under N2 for 3 hours. After 3 hours, a solution of 1.5 eq of freshly distilled 3-N,N-dimethylaminopropyl chloride (9.83 g) dissolved in 25 ml THF was added dropwise and the reaction then heated at reflux overnight.

Workup

  1. additionIn a 500 ml flask was added 0.88 g
  2. washof freshly washed (with hexane) KH (2.2 eq, 22 mmoles)
  3. temperaturethe contents were heated
  4. temperatureat reflux under N2 for 3 hours
  5. additionwas added dropwise
  6. customthe reaction
  7. temperaturethen heated
  8. temperatureat reflux overnight

Sources & evidence

ORD record
ord-04cfff75b8cb4595be90f27ffcf6e916
Source dataset
uspto-grants-1986_06
Patent number
US04595759

Reaction notes

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