Triethylamine → HCID 22160711, compound

HRID 1089187Notes

Reaction equation

HRID 1089187 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:20](Cl)(=[O:25])[CH2:21][CH:22]([CH3:24])[CH3:23]>C(Cl)Cl>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:20](=[O:25])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66054Isovaleryl chlorideHCID 75467Benzenemethanamine, N-butyl-

Product 1

HCID 22160711HCID 22160711, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 6.0 g of N-benzyl-n-butylamine in 3 ml of methylene chloride containing 4.5 ml of triethylamine, under inert gas, was cooled to 0° C. and treated by the dropwise addition of 4.27 ml of iso-valerylchloride. Another 3 ml of methylene chloride was added and stirred at ambient temperature for 18 hours. The insolubles were filtered and the cake washed with methylene chloride. The combined filtrates were washed with water, brine and dried. Evaporation of the volatiles gave a brown oil which was purified by chromatography on silica gel using 1:8 ethyl acetate:-hexanes giving 7.75 g of the desired product as a yellowish oil.

Workup

  1. filtrationThe insolubles were filtered
  2. washthe cake washed with methylene chloride
  3. washThe combined filtrates were washed with water, brine
  4. customdried
  5. customEvaporation of the volatiles
  6. customgave a brown oil which
  7. customwas purified by chromatography on silica gel using 1:8 ethyl acetate

Sources & evidence

ORD record
ord-e007f968ee7a44b5886ff44bde78e93a
Source dataset
uspto-grants-1990_10
Patent number
US04965284

Reaction notes

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