Triethylamine → HCID 54534260, compound

HRID 2073645Notes

Reaction equation

HRID 2073645 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)(=[O:14])[CH:12]=[CH2:13].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([CH:13]=[CH:12][C:11]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 114644-Bromobenzoic acidHCID 3504731-(piperidin-1-yl)prop-2-en-1-one

Product 1

HCID 54534260HCID 54534260, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolvent

Procedure

The acid chloride of the formula (500) and the corresponding free acid are novel and can be prepared as follows: 20.12 g (0.1 mol) of 4-bromobenzoic acid, 17.38 g (125 mmols) of acrylic acid piperidide, 25.28 g (250 mmols) of triethylamine, 0.224 g (1 mmol) of palladium acetate and 1.216 g (4 mmols) of tri-o-tolylphosphine are stirred at 115° C. for 15 minutes. The mixture is stirred with 300 ml of 2N hydrochloric acid and the crude product is filtered off. It is dissolved in 200 ml of 2N sodium hydroxide solution and the solution is filtered. 26 ml of 10N hydrochloric acid are added to the filtrate. The precipitate is filtered off, washed with water and dried. 25.27 g (98% of theory) of 4-carboxycinnamic acid piperidide are obtained in the form of white crystals; melting point 257.1° C.

Workup

  1. customcan be prepared
  2. filtrationthe crude product is filtered off
  3. dissolutionIt is dissolved in 200 ml of 2N sodium hydroxide solution
  4. filtrationthe solution is filtered
  5. addition26 ml of 10N hydrochloric acid are added to the filtrate
  6. filtrationThe precipitate is filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-1eb5309e52874a61a34d7a938de6d754
Source dataset
uspto-grants-1990_04
Patent number
US04918215

Reaction notes

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