Hydrochloric Acid → HCID 22634635, compound

HRID 2417342Notes

Reaction equation

HRID 2417342 reaction equation
[CH2:1]([NH2:3])[CH3:2].[CH3:4][C:5]1[C:6]([C:19]2[CH:20]=[C:21](C=CC(Cl)=O)[CH:22]=[CH:23][CH:24]=2)=[CH:7][C:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1.Cl.[CH2:31]1C[O:34][CH2:33][CH2:32]1>>[CH2:1]([NH:3][C:33](=[O:34])[C:32]([C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:6]2[C:5]([CH3:4])=[CH:14][C:13]3[C:12]([CH3:16])([CH3:15])[CH2:11][CH2:10][C:9]([CH3:18])([CH3:17])[C:8]=3[CH:7]=2)[CH:20]=1)=[CH2:31])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 8028Tetrahydrofuran2×HCID 53728690HCID 53728690, compound

Product 1

HCID 22634635HCID 22634635, compound

Procedure

20 ml of THF are introduced into a round-bottomed flask and 2.8 ml (35 mmol) of ethylamine solution (70%) are added. A solution of 1.2 g (3.2 mmol) of 3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenylacryloyl chloride in 40 ml of THF is added dropwise and the mixture is stirred at room temperature for one hour. The reaction medium is acidified with hydrochloric acid and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with dichloromethane. After evaporation of the solvents, 817 mg (68%) of N-ethyl-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-phenylacrylamide are collected, with a melting point of 158-9° C.

Workup

  1. extractionextracted with ethyl ether
  2. customthe organic phase is separated out after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with dichloromethane
  8. customAfter evaporation of the solvents, 817 mg (68%) of N-ethyl-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-phenylacrylamide
  9. customare collected, with a melting point of 158-9° C.

Sources & evidence

ORD record
ord-4a905cf33697401e90b8c64ace196cac
Source dataset
uspto-grants-2004_11
Patent number
US06825360B1

Reaction notes

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