Triethylamine → HCID 19970138, compound

HRID 975083Notes

Reaction equation

HRID 975083 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH2:10][C:11]1([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:15][CH2:14][NH:13][CH2:12]1.[CH:24]([O:27][C:28]1[CH:29]=[C:30]([CH2:34][C:35](O)=[O:36])[CH:31]=[CH:32][CH:33]=1)([CH3:26])[CH3:25]>C(Cl)Cl>[OH:8][CH2:9][CH2:10][C:11]1([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:15][CH2:14][N:13]([C:35](=[O:36])[CH2:34][C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([O:27][CH:24]([CH3:25])[CH3:26])[CH:29]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 166389242-(3-(Propan-2-yloxy)phenyl)acetic acidHCID 184644272-(3-(3,4-Dichlorophenyl)pyrrolidin-3-yl)ethanol

Product 1

HCID 19970138HCID 19970138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (22.5 ml) and 3-(2-hydroxyethyl)-3-(3,4-dichlorophenyl)pyrrolidine (22 grams) are added to a solution of 16 grams of 3-isopropoxyphenylacetic acid in 500 ml of methylene chloride. The mixture is cooled to 0° C. and 42.6 grams of benzotriazolyl-N-oxytrisdimethylaminophosphonium hexafluorophosphate are then added and the reaction mixture is allowed to warm up to room temperature. After thirty minutes, the mixture is concentrated under vacuum and the residue is taken up in diethyl ether and washed successively with water, a dilute sodium hydroxide solution, a saturated sodium chloride solution, a dilute hydrochloric acid solution, a saturated sodium chloride solution, and a solution of sodium bicarbonate. The organic fraction is dried over magnesium sulfate, filtered, and concentrated in vacuo to yield the title intermediate.

Workup

  1. temperatureto warm up to room temperature
  2. waitAfter thirty minutes
  3. concentrationthe mixture is concentrated under vacuum
  4. washwashed successively with water
  5. dry with materialThe organic fraction is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47e3507dde1c40ab979675b7641736fa
Source dataset
uspto-grants-1997_03
Patent number
US05607947

Reaction notes

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