Dimethylamine → HCID 54184450, compound

HRID 1085664Notes

Reaction equation

HRID 1085664 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]1([CH2:13][CH:14]=[CH:15][CH2:16][C@@H:17]([CH:21]([CH3:23])[CH3:22])[C:18](O)=[O:19])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:24][NH:25][CH3:26].N1C=CC=CC=1>C(Cl)Cl.CCOCC.CN(C=O)C.C1(C)C=CC=CC=1>[CH3:24][N:25]([CH3:26])[C:18](=[O:19])[C@H:17]([CH:21]([CH3:23])[CH3:22])[CH2:16][CH:15]=[CH:14][CH2:13][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

9

Reactant 4

HCID 674DimethylamineHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 54462552HCID 54462552, compound

Product 1

HCID 54184450HCID 54184450, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

42.6 ml (0.49 mol) of oxalyl chloride are metered into a solution of 58.1 g (0.244 mol) of 6-cyclohexyl-2(S)-isopropyl-4-hexenoic acid in 270 ml of abs. toluene and 0.5 ml of DMF. When the addition is complete, the reaction mixture is boiled under reflux for 90 minutes, then concentrated in a rotary evaporator. The residue is dissolved in 270 ml of dry CH2Cl2 and added dropwise, at 0° , to a solution of 17.2 g (0.38 mol) of dimethylamine and 61.4 ml (0.76 mol) of pyridine in 270 ml of CH2Cl2. After stirring for 30 minutes at 0°, the mixture is diluted with ether and washed twice with 2N HCl, twice with saturated NaHCO3 solution and twice with brine. The combined organic phases are dried with MgSO4 and concentrated by evaporation. The residue is distilled at 124°-128°/0.04 mbar.

Workup

  1. additionWhen the addition
  2. temperatureunder reflux for 90 minutes
  3. concentrationconcentrated in a rotary evaporator
  4. dissolutionThe residue is dissolved in 270 ml of dry CH2Cl2
  5. washwashed twice with 2N HCl, twice with saturated NaHCO3 solution and twice with brine
  6. dry with materialThe combined organic phases are dried with MgSO4
  7. concentrationconcentrated by evaporation
  8. distillationThe residue is distilled at 124°-128°/0.04 mbar

Sources & evidence

ORD record
ord-32a325867e004a86bcf4c87dd5fd61e4
Source dataset
uspto-grants-1991_04
Patent number
US05010189

Reaction notes

Loading…