Ethanol → HCID 178442730, compound

HRID 1153915Notes

Reaction equation

HRID 1153915 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C([O:8][C:9]1[C:14]2[CH:15]([C:21]#[N:22])[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:13]=2[CH:12]=[C:11]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1)(=O)C.C(O)C.Cl.CN1CCCCC1>CN1CCCCC1>[OH:8][C:9]1[C:14]2[CH:15]([C:21]3[NH:22][N:3]=[N:2][N:1]=3)[CH2:16][C:17]([CH3:19])([CH3:20])[O:18][C:13]=2[CH:12]=[C:11]([C:23]([CH3:30])([CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 33557Sodium AzideHCID 205378Piperidine, 1-methyl-, hydrochlorideHCID 19848841HCID 19848841, compound

Product 1

HCID 178442730HCID 178442730, compound

Reagents, catalysts & solvents 1

HCID 12291N-MethylpiperidineCatalyst

Procedure

Finely ground sodium azide (325 mg, 5 mmole) is added to a solution of 5-acetoxy-4-cyano-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran (1.855 g, 5 mmole) in 10 ml ethanol-free chloroform containing 271 mg (2 mmole) N-methylpiperidine hydrochloride and 5 drops of N-methylpiperidine. The mixture is heated at reflux for one hour, another 2 mmoles of N-methylpiperidine hydrochloride is added, refluxing is continued for one hour and the mixture is allowed to stand overnight at room temperature. The mixture is partitioned between chloroform and aqueous sodium carbonate solution, the aqueous phase is adjusted to pH 5 and extracted again with chloroform. The combined organic layers are washed with water, dried (MgSO4) and the solvent evaporated in vacuo to afford the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for one hour
  3. temperaturerefluxing
  4. waitto stand overnight at room temperature
  5. customThe mixture is partitioned between chloroform and aqueous sodium carbonate solution
  6. extractionextracted again with chloroform
  7. washThe combined organic layers are washed with water
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-cda9c3f2322b43f8901cf82a0df219f0
Source dataset
uspto-grants-1984_12
Patent number
US04486428

Reaction notes

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