Boron tribromide → HCID 20460577, compound

HRID 27172Notes

Reaction equation

HRID 27172 reaction equation
Cl.Cl.[C:3]1([CH3:25])[CH:8]=[CH:7][C:6]([NH:9][CH2:10][CH:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23]C)=[C:18]([O:21]C)[CH:19]=3)[CH2:14][CH2:13][NH:12]2)=[CH:5][CH:4]=1.B(Br)(Br)[Br:27]>ClCCl>[BrH:27].[BrH:27].[C:3]1([CH3:25])[CH:4]=[CH:5][C:6]([NH:9][CH2:10][CH:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:23])=[C:18]([OH:21])[CH:19]=3)[CH2:14][CH2:13][NH:12]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 204605361-(p-Toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride

Product 1

HCID 20460577HCID 20460577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(p-Toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (260 mg) was converted into the free amine compound by conventional methods. The amine compound was dissolved in anhydrous dichloromethane (10 ml) and to the solution was dropwise added at -50° C. anhydrous dichloromethane (5 ml) containing boron tribromide (340 mg). The mixture was stirred for 14 hours at the same temperature and the reaction temperature was gradually elevated to 8° C. The reaction mixture was concentrated to dryness under reduced pressure and the residue obtained was crystallized with acetone. The crystals were further recrystallized from a mixture of isopropyl alcohol and ether to give 1-(p-toluidinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrobromide, mp 211° to 213° C. The product was identified by means of comparison with an authentic sample required by another process by its infrared absorption spectrum and nuclear magnetic resonance spectrum.

Workup

  1. customwas gradually elevated to 8° C
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. customthe residue obtained
  4. customwas crystallized with acetone
  5. customThe crystals were further recrystallized from a mixture of isopropyl alcohol and ether

Sources & evidence

ORD record
ord-965d3f331bda4a668cdec79984ae765a
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Reaction notes

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