Hydrochloric Acid → HCID 45263090, compound

HRID 27246Notes

Reaction equation

HRID 27246 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:23][CH2:22][C:21]2[C:16](=[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:18]=[CH:19][CH:20]=2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].[ClH:33]>CCOCC.O.O1CCCC1>[ClH:33].[CH2:7]([N:14]1[CH2:23][CH2:22][C:21]2[C:16](=[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 233443172-Benzyl-8-phenyl-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 45263090HCID 45263090, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3.6 Parts of lithium aluminum hydride is added to a solution of 10 parts of 2-benzyl-3,4-dihydro-8-phenyl-1(2H)-isoquinolone in 225 parts by volume dry tetrahydrofuran and the resulting mixture is stirred at reflux temperature for about 5 hours. Then the mixture is cooled in an ice bath and treated successively with 7.5 parts by volume of water in 15 parts by volume of tetrahydrofuran, 7.5 parts by volume of 25% sodium hydroxide, and 7.5 parts by volume of water. The salts which form are filtered off and the filtrate is dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield clear oil. The oil is taken up in ether and treated with isopropanolic hydrogen chloride to give, as a white solid, 2-benzyl-8-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride, melting at about 187°-189° C. after recrystallization from a mixture of ethanol and ether. This compound has the following formula ##STR16##

Workup

  1. temperatureat reflux temperature for about 5 hours
  2. temperatureThen the mixture is cooled in an ice bath
  3. filtrationThe salts which form are filtered off
  4. dry with materialthe filtrate is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield clear oil

Sources & evidence

ORD record
ord-4ce3cf20126c41bb873dee78da9b6aa0
Source dataset
uspto-grants-1980_09
Patent number
US04220778

Reaction notes

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