Dodecylamine → HCID 18319119, compound

HRID 1383941Notes

Reaction equation

HRID 1383941 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][C:12]([OH:14])=O)=[CH:8][CH:7]=1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[CH2:38]([NH2:50])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]>O1CCCC1.C(OCC)(=O)C>[CH2:38]([NH:50][C:12](=[O:14])[CH2:11][O:10][C:9]1[CH:8]=[CH:7][C:6](/[CH:5]=[CH:4]/[C:3](=[O:17])[C:2]([F:1])([F:19])[F:18])=[CH:16][CH:15]=1)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

6

Reactant 3

HCID 13583DodecylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 18319070HCID 18319070, compound

Product 1

HCID 18319119HCID 18319119, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-4-(4,4,4-trifluoro-3-oxo-1-butenyl)phenoxyacetic acid (0.810 g, 2.95 mmol) in tetrahydrofuran (20 ml) was treated with EEDQ (0.767 g, 3.10 mmol) and dodecylamine (0.575 g, 3.10 mmol). After 2 h at 22° C., the reaction mixture was diluted with ethyl acetate, washed with water, 0.1N hydrochloric acid, saturated sodium bicarbonate, brine and dried. Evaporation of the solvent under reduced pressure gave a solid which was chromatographed on silica gel. Elution with a mixture of toluene and ethyl acetate (8:12) gave 0.750 g (58%) of the title material as white needles after recrystallization from ethyl acetate-hexane: mp 78.5-79° C.

Workup

  1. washwashed with water, 0.1N hydrochloric acid, saturated sodium bicarbonate, brine
  2. customdried
  3. customEvaporation of the solvent under reduced pressure
  4. customgave a solid which
  5. customwas chromatographed on silica gel
  6. washElution
  7. additionwith a mixture of toluene and ethyl acetate (8:12)

Sources & evidence

ORD record
ord-81d140fd8257460684fdce6455875b85
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

Loading…