Hydrochloric Acid → HCID 21996630, compound

HRID 1977982Notes

Reaction equation

HRID 1977982 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([C:16]#[C:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]3([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:21][CH2:20]2)[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[OH-].[Na+]>CO>[ClH:3].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][C:22]3([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:23][CH2:24]2)[CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 21996598HCID 21996598, compound

Product 1

HCID 21996630HCID 21996630, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 g of the hydrochloride of the acetylene compound obtained in Example 1 are liberated with aqueous 10% sodium hydroxide solution. The oil obtained after extraction with diethyl ether is washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated under vacuum. The residual oil is then taken up in 100 ml of ethyl acetate, after which 5 ml of methanol are added, followed by 0.2 g of Pd/BaSO4, and the reaction mixture is hydrogenated at room temperature and at atmospheric pressure. The catalyst is separated out by filtration through Celite and the filtrate is concentrated under vacuum. The residue obtained is taken up in the minimum amount of methanol in the presence of 50 ml of 2 N hydrochloric acid and is then successively extracted with dichloromethane, washed with 2N hydrochloric acid solution, with saturated sodium chloride solution, dried over magnesium sulphate and concentrated under vacuum in order to obtain 2 g of the expected hydrochloride; m.p.=266° C.

Workup

  1. customThe oil obtained
  2. extractionafter extraction with diethyl ether
  3. washis washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under vacuum
  6. additionafter which 5 ml of methanol are added
  7. customis hydrogenated at room temperature and at atmospheric pressure
  8. customThe catalyst is separated out by filtration through Celite
  9. concentrationthe filtrate is concentrated under vacuum
  10. customThe residue obtained
  11. extractionis then successively extracted with dichloromethane
  12. washwashed with 2N hydrochloric acid solution, with saturated sodium chloride solution
  13. dry with materialdried over magnesium sulphate
  14. concentrationconcentrated under vacuum in order

Sources & evidence

ORD record
ord-8398558856694eceb19aa7c41019eb0b
Source dataset
uspto-grants-2001_05
Patent number
US06235791B1

Reaction notes

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