Sodium Azide → HCID 178442109, compound

HRID 1632588Notes

Reaction equation

HRID 1632588 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C([O:8][C:9]1[CH:18]=[C:17]([O:19][CH:20]([CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:21])[CH:16]=[C:15]2[C:10]=1[CH:11]([CH2:35][CH2:36][C:37]#[N:38])[CH2:12][CH:13]1[CH2:34][CH2:33][CH2:32][CH2:31][N:14]12)(=O)C.Cl.CN1CCCCC1>CN1CCCCC1.C(O)C>[OH:8][C:9]1[CH:18]=[C:17]([O:19][CH:20]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:21])[CH:16]=[C:15]2[C:10]=1[CH:11]([CH2:35][CH2:36][C:37]1[NH:38][N:3]=[N:2][N:1]=1)[CH2:12][CH:13]1[CH2:34][CH2:33][CH2:32][CH2:31][N:14]12

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 205378Piperidine, 1-methyl-, hydrochloride2×HCID 20443048HCID 20443048, compound

Product 1

HCID 178442109HCID 178442109, compound

Reagents, catalysts & solvents 2

HCID 12291N-MethylpiperidineCatalystHCID 702EthanolSolvent

Procedure

Finely ground sodium azide (325 mg., 5 mmole) is added to a solution of 7-acetoxy-6-(2-cyanoethyl)-9-(5-phenyl-2-pentyloxy)-2,3,4,4a,5,6-hexahydro-1H-pyrido-[1,2-a]quinoline (506 mg., 1 mmole) in 5 ml. of ethanol-free chloroform containing 271 mg. (2 mmole) N-methyl-piperidine hydrochloride and 5 drops of N-methylpiperidine. The mixture is heated at reflux for one hour, another 2 mmole of N-methylpiperidine hydrochloride is added, refluxing continued for another hour and allowed to stand overnight at room temperature. The mixture is partitioned between chloroform and aqueous sodium carbonate solution. The aqueous layer is adjusted to pH 5, extracted again with chloroform and the combined organic layers washed with water and the chloroform is dried (MgSO4) Evaporation of solvent under reduced pressure affords the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for one hour
  3. temperaturerefluxing
  4. waitcontinued for another hour
  5. customThe mixture is partitioned between chloroform and aqueous sodium carbonate solution
  6. extractionextracted again with chloroform
  7. washthe combined organic layers washed with water
  8. dry with materialthe chloroform is dried
  9. custom(MgSO4) Evaporation of solvent under reduced pressure

Sources & evidence

ORD record
ord-7ecb5768f8014ef78153b7545a2ef944
Source dataset
uspto-grants-1984_10
Patent number
US04476131

Reaction notes

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