Hydrochloric Acid → HCID 606145, compound

HRID 1414277Notes

Reaction equation

HRID 1414277 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:15][CH2:16][NH2:17].Cl.[OH-].[Na+]>>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1)[NH:17][CH2:16][CH2:15]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8421HomoveratrylamineHCID 14798Sodium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 606145HCID 606145, compound

Procedure

50 parts of p-fluorobenzaldehyde and 65 parts of 3,4-dimethoxyphenethylamine are combined and heated over a steam bath in a nitrogen atmosphere for 90 minutes. Then 800 parts by volume of 20% by weight hydrochloric acid is added and heating is continued for an additional 3 hours. The reaction mixture is cooled, made alkaline with sodium hydroxide and extracted with methylene chloride. The organic layer is dried over anhydrous calcium sulfate and stripped in vacuo to give 6,7-dimethoxy-1-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline. After crystallization from a mixture of ethyl ether and n-hexane, that product melts at about 145°-150°C.

Workup

  1. temperatureheated over a steam bath in a nitrogen atmosphere for 90 minutes
  2. temperatureheating
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer is dried over anhydrous calcium sulfate

Sources & evidence

ORD record
ord-a9593398e4a94a2289b99bd7caaa728b
Source dataset
uspto-grants-1977_01
Patent number
US04001244

Reaction notes

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