Triethylamine → N-ethyl-N-cyclohexyl-5-(1-cyclohexyl-1,2,3,4-tetrazol-5-yl)valeramide

HRID 978032Notes

Reaction equation

HRID 978032 reaction equation
[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:34]([NH:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[CH3:35]>O1CCCC1>[CH2:34]([N:36]([CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1[N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[N:8]=[N:9][N:10]=1)[CH3:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21609N-Ethyl cyclohexylamineHCID 62365Isobutyl chloroformateHCID 132034025-(1-Cyclohexyl-1,2,3,4-tetrazol-5-yl)valeric acid

Product 1

HCID 13203397N-ethyl-N-cyclohexyl-5-(1-cyclohexyl-1,2,3,4-tetrazol-5-yl)valeramideYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(1-Cyclohexyl-1,2,3,4-tetrazol-5-yl)valeric acid (2.4 g) is dissolved in tetrahydrofuran (50 ml), and thereto is added triethylamine (1.1 g). To the mixture is added dropwise with stirring isobutyl chloroformate (1.5 g) under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. To the mixture is added dropwise with stirring N-ethyl-cyclohexylamine (1.5 g) at room temperature, and the mixture is further stirred for 2 hours. After distilling off tetrahydrofuran, water is added to the residue, and the mixture is extracted with chloroform. The chloroform layer is washed with an aqueous saturated sodium chloride solution and dried over magnesium sulfate. Chloroform is distilled off, and the resulting residue is subjected to column chromatography (Kieselgel 60, made by Merck & Co., eluting solvent, chloroform) to isolate N-ethyl-N-cyclohexyl-5-(1-cyclohexyl-1,2,3,4-tetrazol-5-yl)valeramide (2.6 g), white crystalline powder (ether), m.p. 92°-95° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture is further stirred for 2 hours
  3. distillationAfter distilling off tetrahydrofuran, water
  4. additionis added to the residue
  5. extractionthe mixture is extracted with chloroform
  6. washThe chloroform layer is washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. distillationChloroform is distilled off
  9. washthe resulting residue is subjected to column chromatography (Kieselgel 60, made by Merck & Co., eluting solvent, chloroform)

Sources & evidence

ORD record
ord-31c072aa22fb4fdd875781c1ba6b6dec
Source dataset
uspto-grants-1987_05
Patent number
US04663323

Reaction notes

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