Dichloromethane → HCID 67214322, compound

HRID 2421612Notes

Reaction equation

HRID 2421612 reaction equation
[CH2:1]([NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)[CH2:2][CH3:3].[C:14]1([C:20]#[CH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1CCCCC1.C(Cl)Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:1]([NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:21]#[C:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8082PiperidineHCID 10821PhenylacetyleneHCID 31133444-bromo-N-propylbenzamide

Product 1

HCID 67214322HCID 67214322, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of N-n-propyl-4-bromobenzamide from Example 9A, phenylacetylene (1.5 eq.) and Pd(PPh3)2Cl2 (5 mol %) in piperidine (3 eq.) was heated at 70° C. for 30 minutes in a sealed tube. The solidified residue was dissolved with CH2Cl2 and water and poured onto HCl 2N. The acidic phase was extracted three times with CH2Cl2. The combined organic layers were washed once with HCl 2N, twice with saturated NaHCO3, once with water and once with brine. The organic layer was then dried over MgSO4 and concentrated. The resulting residue was purified using SiO2 with CH2Cl2/petroleum ether 80:20 to CH2Cl2 100% to give N-n-propyl-3-phenylethynyl-benzamide as a yellow solid (Quantitative yield). NMR 1H (ppm, CDCl3): 7.73 (d. J3=8.4 Hz, 2H), 7.63-7.51 (m, 5H), 7.36-7.32 (m, 2H), 6.10 (br. s., 1H), 3.45-3.37 (m, 2H), 1.64 (sext., J=7.2 Hz, 2H), 0.99 (t, J3=7.4 Hz, 3H).

Workup

  1. additionpoured onto HCl 2N
  2. extractionThe acidic phase was extracted three times with CH2Cl2
  3. washThe combined organic layers were washed once with HCl 2N, twice with saturated NaHCO3, once with water and once with brine
  4. dry with materialThe organic layer was then dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-ee2503c250524145b64f2865d50ac40e
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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