Tributylamine → HCID 85705188, compound

HRID 1818967Notes

Reaction equation

HRID 1818967 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O.[CH2:15]([N:19](CCCC)CCCC)[CH2:16][CH2:17][CH3:18].C(N)CCC>C(Cl)Cl>[CH2:15]([NH:19][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 7622TributylamineHCID 8007ButylamineHCID 1781211-Bromoundecanoic acid

Product 1

HCID 85705188HCID 85705188, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

11-Bromoundecanoic acid (45 mmol) was dissolved in dry CH2Cl2 (200 ml) and tributylamine (54 mmol). After the mixture had cooled at −10° C., isobutylchlorofomate (60 mmol) was added and allowed to react for 2 hrs. At this moment, excess N-butylamine (225 mmol) was added and later the cooling bath was removed. After 3 hrs, CH2Cl2 was added and the organic phase was washed with 1 N HCl, saturated NaHCO3, and water. After drying by MgSO4, the solvent was removed and the crude product was purified by column chromatography. The pure amide product was eluted with solvent, hexane (80)—EtOAc (20).

Workup

  1. additionisobutylchlorofomate (60 mmol) was added
  2. customto react for 2 hrs
  3. customlater the cooling bath was removed
  4. additionCH2Cl2 was added
  5. washthe organic phase was washed with 1 N HCl, saturated NaHCO3, and water
  6. dry with materialAfter drying by MgSO4
  7. customthe solvent was removed
  8. customthe crude product was purified by column chromatography
  9. washThe pure amide product was eluted with solvent, hexane (80)—EtOAc (20)

Sources & evidence

ORD record
ord-af535f100b604bb0b39af071c73e7a36
Source dataset
uspto-grants-2009_10
Patent number
US07601739B2

Reaction notes

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