Hydrochloric Acid → HCID 15132179, compound

HRID 1886450Notes

Reaction equation

HRID 1886450 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[C:10]=1[CH3:16].[CH:17](N1CCCCC1)=[O:18].Cl>O1CCCC1.BrC(Br)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:17]=[O:18])[C:10]=1[CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 174291-PiperidinecarboxaldehydeHCID 15132178HCID 15132178, compound

Product 1

HCID 15132179HCID 15132179, compound

Reagents, catalysts & solvents 2

HCID 112011,1-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

1.2 g of Mg (magnesium turnings) in 15 ml of absolute tetrahydrofuran are initially taken under a nitrogen atmosphere. A few drops of dibromoethane are added at 65° C. A solution of 14.25 g of 3-bromo-2-methylbenzyl tetrahydro-2-pyranyl ether in 50 ml of tetrahydrofuran is added dropwise while the temperature is kept at 65° C. The stirred mixture is then refluxed for 2 hours. A solution of 5.65 g of N-formylpiperidine in 10 ml of absolute tetrahydrofuran is added dropwise to the reaction mixture, which has been cooled to 0° C. Stirring is carried out for 20 hours at room temperature and the mixture is rendered slightly acidic with about 50 ml of 5% strength hydrochloric acid and is extracted several times with ether. The combined ether extracts are washed with water, dried and evaporated down. The crude product (11 g) can be purified by column chromatography over silica gel using 97.5:2.5 toluene/acetone.

Workup

  1. customis kept at 65° C
  2. temperatureThe stirred mixture is then refluxed for 2 hours
  3. extractionis extracted several times with ether
  4. washThe combined ether extracts are washed with water
  5. customdried
  6. customevaporated down
  7. customThe crude product (11 g) can be purified by column chromatography over silica gel using 97.5:2.5 toluene/acetone

Sources & evidence

ORD record
ord-d3b655cc4a564d2f805a70036682f6d5
Source dataset
uspto-grants-1992_09
Patent number
US05151441

Reaction notes

Loading…