Benzylamine → HCID 20277898, compound

HRID 1248433Notes

Reaction equation

HRID 1248433 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([N+:26]([O-:28])=[O:27])([CH3:25])[CH2:11][CH2:12][CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O>C(N(CC)CC)C>[CH2:1]([NH:8][CH2:13][CH2:12][CH2:11][C:10]([CH3:25])([N+:26]([O-:28])=[O:27])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 20277890HCID 20277890, compound

Product 1

HCID 20277898HCID 20277898, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred mixture of benzylamine (9 ml) and triethylamine (5.5 ml) was added 4-methyl-4-nitro-1-tosyloxypentane (11.9 gm). The mixture was then heated to 70° C. for 2 hrs. The mixture was cooled and partitioned between ethyl acetate and water, the ethyl acetate solution was washed twice with water, then with brine and dried over magnesium sulphate. The solution was evaporated and the product isolated by column chromatography of the residue using gradient elution (Kieselgel; 1:1 60/80 petroleum ether:ethyl acetate going to ethyl acetate). Yield 6.89 gm.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washthe ethyl acetate solution was washed twice with water
  4. dry with materialwith brine and dried over magnesium sulphate
  5. customThe solution was evaporated
  6. customthe product isolated by column chromatography of the residue
  7. washelution (Kieselgel; 1:1 60/80 petroleum ether:ethyl acetate going to ethyl acetate)

Sources & evidence

ORD record
ord-3fbd15bb4c1d4520879af44ca982aae0
Source dataset
uspto-grants-1985_06
Patent number
US04524073

Reaction notes

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